Merge remote-tracking branch 'origin/main' into dev

Restore dropped regression fixes
Fix remaining CI regressions
2026-06-16 17:55:26 -04:00 · 2026-06-09 10:41:48 +09:00 · 2026-06-09 10:31:43 +09:00 · 2026-06-09 10:21:56 +09:00 · 2026-06-09 02:20:59 +01:00 · 2026-06-09 10:16:38 +09:00
366 changed files with 33243 additions and 4476 deletions
@@ -56,6 +56,13 @@ SEARXNG_INSTANCE=http://localhost:8080
 # SQLite database path (default: sqlite:///./data/app.db)
 # DATABASE_URL=sqlite:///./data/app.db

+# ============================================================
+# Data directory
+# ============================================================
+# Move everything that lives under data/ - settings, sessions, database, auth,
+# cache, uploads, etc. - to another path:
+# ODYSSEUS_DATA_DIR=C:\path\to\dir
+
 # ============================================================
 # Auth & Security
 # ============================================================
@@ -112,6 +119,9 @@ SEARXNG_INSTANCE=http://localhost:8080
 # Default: http://{LLM_HOST}:11434/v1/embeddings (ollama)
 # EMBEDDING_URL=http://localhost:11434/v1/embeddings

+# Embedding API key (if there's one)
+# EMBEDDING_API_KEY=embedding_api_key_here
+
 # Embedding model name (must be available at the endpoint above)
 # EMBEDDING_MODEL=all-minilm:l6-v2

@@ -144,6 +154,21 @@ SEARXNG_INSTANCE=http://localhost:8080
 # if you intentionally want scheduled scripts to run remotely.
 # ODYSSEUS_SCRIPT_HOST=localhost

+# Chat / agent attachment size cap in bytes (default: 10 MB).
+# Raise this for local installs that need larger PDFs or text documents.
+# Example: 52428800 = 50 MB.
+# ODYSSEUS_CHAT_UPLOAD_MAX_BYTES=10485760
+
+# Other per-feature upload size caps in bytes. All are validated and optional;
+# defaults shown. An invalid value (non-integer or < 1) fails fast at startup.
+# ODYSSEUS_GALLERY_UPLOAD_MAX_BYTES=104857600            # gallery image upload (100 MB)
+# ODYSSEUS_GALLERY_TRANSFORM_UPLOAD_MAX_BYTES=26214400   # gallery transform input (25 MB)
+# ODYSSEUS_MEMORY_IMPORT_MAX_BYTES=10485760              # memory import file (10 MB)
+# ODYSSEUS_PERSONAL_UPLOAD_MAX_BYTES=26214400            # personal document upload (25 MB)
+# ODYSSEUS_EMAIL_COMPOSE_UPLOAD_MAX_BYTES=26214400       # email compose attachment (25 MB)
+# ODYSSEUS_STT_MAX_AUDIO_BYTES=26214400                  # speech-to-text audio (25 MB)
+# ODYSSEUS_ICS_MAX_BYTES=10485760                        # calendar .ics import (10 MB)
+
 # ============================================================
 # GPU support (Docker Compose)
 # ============================================================
@@ -23,7 +23,7 @@ body:
          required: true
        - label: This is **not** a security vulnerability. (Vulnerabilities go to [GitHub Security Advisories](https://github.com/pewdiepie-archdaemon/odysseus/security/advisories/new) — see [SECURITY.md](https://github.com/pewdiepie-archdaemon/odysseus/blob/main/SECURITY.md).)
          required: true
-        - label: I am running the latest code from `main`.
+        - label: I am running the latest code from the `dev` branch (the default branch you get on clone, where fixes land first) and the bug still reproduces there. Please `git pull` the latest `dev` before filing.
          required: true

  - type: dropdown
@@ -103,14 +103,21 @@ module.exports = async ({ github, context, core }) => {

  async function swapLabel(num, add, remove) {
    if (await labelExists(add)) {
-      await github.rest.issues.addLabels({ owner, repo, issue_number: num, labels: [add] });
+      try {
+        await github.rest.issues.addLabels({ owner, repo, issue_number: num, labels: [add] });
+      } catch (e) {
+        // Fail soft on a token that can't write labels so a label permission
+        // problem never masks the actual description verdict.
+        if (e.status !== 403) throw e;
+        core.warning(`Could not add "${add}" — token lacks label write here; skipping.`);
+      }
    } else {
      core.warning(`Label "${add}" does not exist in the repo — skipping. Create it once to enable labelling.`);
    }
    try {
      await github.rest.issues.removeLabel({ owner, repo, issue_number: num, name: remove });
    } catch (e) {
-      if (e.status !== 404 && e.status !== 410) throw e;
+      if (e.status !== 404 && e.status !== 410 && e.status !== 403) throw e;
    }
  }

@@ -20,6 +20,8 @@ jobs:
    runs-on: ubuntu-latest
    steps:
      - uses: actions/checkout@34e114876b0b11c390a56381ad16ebd13914f8d5  # v4
+        with:
+          persist-credentials: false
      - uses: actions/setup-python@a26af69be951a213d495a4c3e4e4022e16d87065  # v5
        with:
          python-version: "3.11"
@@ -31,6 +33,8 @@ jobs:
    runs-on: ubuntu-latest
    steps:
      - uses: actions/checkout@34e114876b0b11c390a56381ad16ebd13914f8d5  # v4
+        with:
+          persist-credentials: false
      - uses: actions/setup-node@49933ea5288caeca8642d1e84afbd3f7d6820020  # v4
        with:
          node-version: "20"
@@ -51,10 +55,40 @@ jobs:
    continue-on-error: true
    steps:
      - uses: actions/checkout@34e114876b0b11c390a56381ad16ebd13914f8d5  # v4
+        with:
+          fetch-depth: 0
+          persist-credentials: false
+
+      # Detect whether this PR only touches documentation files.
+      # If so, skip the expensive pytest run while still reporting a passing check.
+      - name: Check for docs-only changes
+        id: docs-check
+        run: |
+          if [ "${{ github.event_name }}" = "pull_request" ]; then
+            BASE="${{ github.event.pull_request.base.sha }}"
+            HEAD="${{ github.event.pull_request.head.sha }}"
+          else
+            BASE="${{ github.event.before }}"
+            HEAD="${{ github.sha }}"
+          fi
+          # List all changed files; if every file matches docs/markdown patterns, skip pytest.
+          changed=$(git diff --name-only "$BASE" "$HEAD" 2>/dev/null || git diff --name-only HEAD~1 HEAD)
+          non_docs=$(echo "$changed" | grep -Ev '^(docs/|.*\.md$|\.github/[^/]+\.md$)' || true)
+          if [ -z "$non_docs" ]; then
+            echo "docs_only=true" >> "$GITHUB_OUTPUT"
+            echo "Docs-only change detected — skipping pytest."
+          else
+            echo "docs_only=false" >> "$GITHUB_OUTPUT"
+          fi
+
      - uses: actions/setup-python@a26af69be951a213d495a4c3e4e4022e16d87065  # v5
+        if: steps.docs-check.outputs.docs_only != 'true'
        with:
          python-version: "3.11"
          cache: pip
      - run: pip install -r requirements.txt
+        if: steps.docs-check.outputs.docs_only != 'true'
      - run: mkdir -p data  # sqlite DB lives at ./data/app.db
+        if: steps.docs-check.outputs.docs_only != 'true'
      - run: python -m pytest -q
+        if: steps.docs-check.outputs.docs_only != 'true'
@@ -0,0 +1,140 @@
+name: ci / docker publish
+
+# Build the Odysseus image and publish to GHCR.
+#   push to main -> :latest, :X.Y.Z            (curated release; main is fast-forwarded at releases)
+#   push to dev  -> :dev,    :X.Y.Z-dev.<sha>  (rolling dev + an immutable, traceable pin)
+# Multi-arch (linux/amd64 + linux/arm64): each arch builds on its own native
+# runner and pushes by digest, then a merge job stitches the digests into one
+# manifest list and applies the tags (faster + cleaner than QEMU emulation).
+# Registry: ghcr.io/<owner>/<repo>.
+
+on:
+  push:
+    branches: [dev, main]
+    paths-ignore:
+      - '**.md'
+      - 'docs/**'
+      - '.github/ISSUE_TEMPLATE/**'
+
+concurrency:
+  group: docker-publish-${{ github.ref }}
+  cancel-in-progress: true
+
+permissions:
+  contents: read
+
+env:
+  REGISTRY: ghcr.io
+  IMAGE_NAME: ${{ github.repository }}
+
+jobs:
+  build:
+    name: build (${{ matrix.arch }})
+    runs-on: ${{ matrix.runner }}
+    permissions:
+      contents: read
+      packages: write
+    strategy:
+      fail-fast: false
+      matrix:
+        include:
+          - platform: linux/amd64
+            arch: amd64
+            runner: ubuntu-latest
+          - platform: linux/arm64
+            arch: arm64
+            runner: ubuntu-24.04-arm
+    steps:
+      - uses: actions/checkout@df4cb1c069e1874edd31b4311f1884172cec0e10  # v6.0.3
+        with:
+          persist-credentials: false
+      - name: Set up Buildx
+        uses: docker/setup-buildx-action@d7f5e7f509e45cec5c76c4d5afdd7de93d0b3df5  # v4.1.0
+      - name: Log in to GHCR
+        uses: docker/login-action@650006c6eb7dba73a995cc03b0b2d7f5ca915bee  # v4.2.0
+        with:
+          registry: ${{ env.REGISTRY }}
+          username: ${{ github.actor }}
+          password: ${{ secrets.GITHUB_TOKEN }}
+      - name: Build and push by digest
+        id: build
+        uses: docker/build-push-action@f9f3042f7e2789586610d6e8b85c8f03e5195baf  # v7.2.0
+        with:
+          context: .
+          platforms: ${{ matrix.platform }}
+          outputs: type=image,name=${{ env.REGISTRY }}/${{ env.IMAGE_NAME }},push-by-digest=true,name-canonical=true,push=true
+          cache-from: type=gha,scope=${{ matrix.arch }}
+          cache-to: type=gha,mode=max,scope=${{ matrix.arch }}
+      - name: Export digest
+        run: |
+          mkdir -p /tmp/digests
+          digest="${{ steps.build.outputs.digest }}"
+          touch "/tmp/digests/${digest#sha256:}"
+      - name: Upload digest
+        uses: actions/upload-artifact@043fb46d1a93c77aae656e7c1c64a875d1fc6a0a  # v7.0.1
+        with:
+          name: digest-${{ matrix.arch }}
+          path: /tmp/digests/*
+          if-no-files-found: error
+          retention-days: 1
+
+  merge:
+    name: merge manifest + tag
+    runs-on: ubuntu-latest
+    needs: build
+    permissions:
+      contents: read
+      packages: write
+    steps:
+      - uses: actions/checkout@df4cb1c069e1874edd31b4311f1884172cec0e10  # v6.0.3
+        with:
+          persist-credentials: false
+      - name: Read APP_VERSION + short sha
+        id: ver
+        run: |
+          v=$(grep -E '^APP_VERSION' src/constants.py | head -1 | sed -E 's/.*"([^"]+)".*/\1/')
+          [ -n "$v" ] || { echo "APP_VERSION not found"; exit 1; }
+          echo "version=$v" >> "$GITHUB_OUTPUT"
+          echo "short=${GITHUB_SHA::7}" >> "$GITHUB_OUTPUT"
+      - name: Download digests
+        uses: actions/download-artifact@3e5f45b2cfb9172054b4087a40e8e0b5a5461e7c  # v8.0.1
+        with:
+          path: /tmp/digests
+          pattern: digest-*
+          merge-multiple: true
+      - name: Set up Buildx
+        uses: docker/setup-buildx-action@d7f5e7f509e45cec5c76c4d5afdd7de93d0b3df5  # v4.1.0
+      - name: Log in to GHCR
+        uses: docker/login-action@650006c6eb7dba73a995cc03b0b2d7f5ca915bee  # v4.2.0
+        with:
+          registry: ${{ env.REGISTRY }}
+          username: ${{ github.actor }}
+          password: ${{ secrets.GITHUB_TOKEN }}
+      - name: Compute tags
+        id: meta
+        uses: docker/metadata-action@80c7e94dd9b9319bd5eb7a0e0fe9291e23a2a2e9  # v6.1.0
+        with:
+          images: ${{ env.REGISTRY }}/${{ env.IMAGE_NAME }}
+          tags: |
+            type=raw,value=latest,enable=${{ github.ref == 'refs/heads/main' }}
+            type=raw,value=${{ steps.ver.outputs.version }},enable=${{ github.ref == 'refs/heads/main' }}
+            type=raw,value=dev,enable=${{ github.ref == 'refs/heads/dev' }}
+            type=raw,value=${{ steps.ver.outputs.version }}-dev.${{ steps.ver.outputs.short }},enable=${{ github.ref == 'refs/heads/dev' }}
+      - name: Create manifest list + push tags
+        working-directory: /tmp/digests
+        run: |
+          tags=$(jq -cr '.tags | map("-t " + .) | join(" ")' <<< "$DOCKER_METADATA_OUTPUT_JSON")
+          digests=$(printf "${REGISTRY}/${IMAGE_NAME}@sha256:%s " *)
+          # word-splitting is intended: $tags and $digests each expand to multiple args
+          # shellcheck disable=SC2086
+          docker buildx imagetools create $tags $digests
+        env:
+          REGISTRY: ${{ env.REGISTRY }}
+          IMAGE_NAME: ${{ env.IMAGE_NAME }}
+      - name: Inspect
+        run: |
+          if [ "$GITHUB_REF" = "refs/heads/main" ]; then ref=latest; else ref=dev; fi
+          docker buildx imagetools inspect "${REGISTRY}/${IMAGE_NAME}:${ref}"
+        env:
+          REGISTRY: ${{ env.REGISTRY }}
+          IMAGE_NAME: ${{ env.IMAGE_NAME }}
@@ -14,10 +14,11 @@ jobs:
    # Skip bots (Dependabot, release-drafter, etc.)
    if: ${{ github.event.issue.user.type != 'Bot' }}
    steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@df4cb1c069e1874edd31b4311f1884172cec0e10  # v6.0.3
        with:
          sparse-checkout: .github/scripts
+          persist-credentials: false

-      - uses: actions/github-script@v7
+      - uses: actions/github-script@3a2844b7e9c422d3c10d287c895573f7108da1b3  # v9.0.0
        with:
          script: return require('./.github/scripts/check-issue-description.js')({github, context, core})
@@ -1,28 +1,109 @@
-name: ci / PR description check
+name: ci / PR checks

 on:
-  pull_request_target:
-    types: [opened, edited, synchronize, reopened]
+  # pull_request_target runs in the base-repo context (has secrets) so the check
+  # works on fork PRs. Safe here: the checkout pins to the base branch (no fork
+  # code runs) and the scripts only read context.payload and call the GitHub API.
+  pull_request_target:  # zizmor: ignore[dangerous-triggers]
+    types: [opened, edited, synchronize, reopened, ready_for_review]

-# pull_request_target runs in the base-repo context (has secrets).
-# The checkout below pins to the base branch so no fork code is executed.
-# The script only reads context.payload and calls the GitHub API.
-permissions:
-  issues: write
-  pull-requests: write
+# Default-deny at the workflow level; each job opts into only the scopes it needs.
+# Note: modifying a PR's labels/comments needs pull-requests:write even though the
+# REST path is under /issues/{n}/...; issues:write alone returns 403 on PRs.
+permissions: {}

 jobs:
  check-description:
    name: Check PR description
    runs-on: ubuntu-latest
-    # Skip bots — they open PRs programmatically and have their own process.
+    permissions:
+      contents: read
+      pull-requests: write
+      issues: write
+    # Skip bots: they open PRs programmatically and have their own process.
    if: github.event.pull_request.user.type != 'Bot'
    steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@df4cb1c069e1874edd31b4311f1884172cec0e10  # v6.0.3
        with:
          ref: ${{ github.base_ref }}
          sparse-checkout: .github/scripts
+          persist-credentials: false

-      - uses: actions/github-script@v7
+      - uses: actions/github-script@3a2844b7e9c422d3c10d287c895573f7108da1b3  # v9.0.0
        with:
          script: return require('./.github/scripts/check-pr-description.js')({github, context, core})
+
+  check-title:
+    name: Check PR title (Conventional Commits)
+    runs-on: ubuntu-latest
+    permissions: {}
+    # Skip bots: they open PRs programmatically and have their own process.
+    if: github.event.pull_request.user.type != 'Bot'
+    steps:
+      - uses: actions/github-script@3a2844b7e9c422d3c10d287c895573f7108da1b3  # v9.0.0
+        with:
+          script: |
+            const title = context.payload.pull_request.title || "";
+            // Conventional Commits: type(optional-scope)(optional !): summary
+            const re = /^(feat|fix|docs|style|refactor|perf|test|build|ci|chore|revert)(\([\w .\/-]+\))?!?: .+/;
+            if (!re.test(title)) {
+              core.setFailed(
+                `PR title is not in Conventional Commits format:\n  "${title}"\n\n` +
+                `Expected: type(scope): summary\n` +
+                `Example:  fix(search): handle empty query\n` +
+                `Types: feat, fix, docs, style, refactor, perf, test, build, ci, chore, revert.`
+              );
+            } else {
+              core.info(`PR title OK: ${title}`);
+            }
+
+  check-mergeable:
+    name: Flag unmergeable PRs
+    runs-on: ubuntu-latest
+    permissions:
+      pull-requests: write
+      issues: write
+    # Skip bots: they open PRs programmatically and have their own process.
+    if: github.event.pull_request.user.type != 'Bot'
+    steps:
+      - uses: actions/github-script@3a2844b7e9c422d3c10d287c895573f7108da1b3  # v9.0.0
+        with:
+          script: |
+            const repo = { owner: context.repo.owner, repo: context.repo.repo };
+            const number = context.payload.pull_request.number;
+            const READY = "ready for review";
+            const CONFLICT = "merge conflict";
+
+            // Ensure the conflict label exists (red). Ignore if already present.
+            try {
+              await github.rest.issues.getLabel({ ...repo, name: CONFLICT });
+            } catch {
+              await github.rest.issues.createLabel({
+                ...repo, name: CONFLICT, color: "B60205",
+                description: "Conflicts with the base branch; needs a rebase before review.",
+              }).catch(() => {});
+            }
+
+            // mergeable is computed asynchronously and is often null right after
+            // an event, so poll a few times until GitHub has resolved it.
+            let pr = null;
+            for (let i = 0; i < 5; i++) {
+              const { data } = await github.rest.pulls.get({ ...repo, pull_number: number });
+              if (data.mergeable !== null) { pr = data; break; }
+              await new Promise(r => setTimeout(r, 3000));
+            }
+            if (!pr || pr.draft) return;
+            const labels = pr.labels.map(l => l.name);
+
+            if (pr.mergeable === false) {
+              if (labels.includes(READY)) {
+                await github.rest.issues.removeLabel({ ...repo, issue_number: number, name: READY }).catch(() => {});
+              }
+              if (!labels.includes(CONFLICT)) {
+                await github.rest.issues.addLabels({ ...repo, issue_number: number, labels: [CONFLICT] });
+              }
+            } else if (pr.mergeable === true) {
+              if (labels.includes(CONFLICT)) {
+                await github.rest.issues.removeLabel({ ...repo, issue_number: number, name: CONFLICT }).catch(() => {});
+              }
+            }
@@ -94,6 +94,18 @@ Before submitting any change that affects what the app looks like — buttons, i

 If you are unsure whether a change is "visual," it is. Default to attaching a screenshot.

+## Code conventions
+
+Don't hardcode values that the project already exposes through a constant or a helper. Hardcoded literals drift out of sync, break on non-default deployments, and reintroduce bugs we've already fixed.
+
+- **Filesystem paths:** never build writable paths from `Path(__file__)...` into the source tree, hardcode `/app/...`, or use a relative `"data/..."` string. Every persisted file and directory has a named constant in `src/constants.py` (for example `AUTH_FILE`, `USER_PREFS_FILE`, `SETTINGS_FILE`, `TTS_CACHE_DIR`, `CHROMA_DIR`). Import and use that named constant; do not re-derive the path locally with `os.path.join(DATA_DIR, "x.json")` or `DATA_DIR / "x.json"`. `DATA_DIR` is the single place that reads `ODYSSEUS_DATA_DIR`, so use it directly only for dynamic paths that have no fixed name (for example per-owner files). If a data file or directory has no constant yet, add one to `src/constants.py`. The source tree is read-only in Docker and `/app/...` does not exist on native runs; guard directory creation so an unwritable path degrades gracefully instead of crashing at import.
+- **Internal API / loopback URLs:** don't hardcode `http://localhost:7000`. Use `internal_api_base()` from `src.constants` (it honors `ODYSSEUS_INTERNAL_BASE` / `APP_PORT`).
+- **Ports, limits, model lists, and similar:** reuse the existing constant if one exists; if it doesn't and the value is used in more than one place, add a constant rather than copying the literal.
+
+If you need a value that has no constant or helper yet, add it to `src/constants.py` (the single source of truth for paths and config; `core/constants.py` only re-exports it for backward compatibility) and import it, rather than repeating a literal across files.
+
+**Commits:** use [Conventional Commits](https://www.conventionalcommits.org), `type(scope): summary` (e.g. `fix(search): ...`, `feat(notes): ...`, `docs(contributing): ...`). Common types: `fix`, `feat`, `refactor`, `docs`, `test`, `chore`, `ci`. Keep the subject short and imperative; put the "why" in the body when it isn't obvious.
+
 ## Issue Reports

 For bugs, include:
@@ -1,5 +1,7 @@
 # Odysseus

+> **Branch note:** `dev` is the default branch and contains the latest development changes, but it may be unstable. For the more stable curated branch, use [`main`](https://github.com/pewdiepie-archdaemon/odysseus/tree/main).
+
 ```
 ───────────────────────────────────────────────
 ⊹ ࣪ ˖ ૮( ˶ᵔ ᵕ ᵔ˶ )っ  Odysseus vers. 1.0
@@ -331,6 +333,12 @@ To expose Odysseus on a local network or Tailscale with HTTPS:
 | `PyMuPDF` | PDF page rendering in the side viewer panel and form-filling. (Note: AGPL-3.0) |
 | `markitdown` | Office/EPUB document text extraction (converts .docx/.xlsx/.pptx/.xls/.epub to Markdown). |

+### Outlook / Office 365 email
+Odysseus email accounts currently use IMAP/SMTP username-password auth. Outlook
+and Microsoft 365 generally require OAuth instead, so normal Microsoft mailbox
+passwords will fail. See [docs/email-outlook.md](docs/email-outlook.md) for the
+current limitation and the planned integration direction.
+
 ## Security Notes
 Odysseus is a self-hosted workspace with powerful local tools: shell access, file uploads, model downloads, web research, email/calendar integrations, and API tokens. Treat it like an admin console.

@@ -394,6 +402,16 @@ Key settings:
 | `CHROMADB_HOST` | `localhost` | ChromaDB host for vector memory. Docker overrides this to `chromadb`. |
 | `CHROMADB_PORT` | `8100` | ChromaDB port for manual host runs. Docker overrides this to `8000`. |
 | `EMBEDDING_URL` | -- | OpenAI-compatible embeddings endpoint |
+| `ODYSSEUS_CHAT_UPLOAD_MAX_BYTES` | `10485760` | Chat/agent attachment cap in bytes. Raise for larger local PDFs or text documents. |
+| `ODYSSEUS_GALLERY_UPLOAD_MAX_BYTES` | `104857600` | Gallery image upload cap in bytes (100 MB). |
+| `ODYSSEUS_GALLERY_TRANSFORM_UPLOAD_MAX_BYTES` | `26214400` | Gallery transform input cap in bytes (25 MB). |
+| `ODYSSEUS_MEMORY_IMPORT_MAX_BYTES` | `10485760` | Memory import file cap in bytes (10 MB). |
+| `ODYSSEUS_PERSONAL_UPLOAD_MAX_BYTES` | `26214400` | Personal document upload cap in bytes (25 MB). |
+| `ODYSSEUS_EMAIL_COMPOSE_UPLOAD_MAX_BYTES` | `26214400` | Email compose attachment cap in bytes (25 MB). |
+| `ODYSSEUS_STT_MAX_AUDIO_BYTES` | `26214400` | Speech-to-text audio cap in bytes (25 MB). |
+| `ODYSSEUS_ICS_MAX_BYTES` | `10485760` | Calendar `.ics` import cap in bytes (10 MB). |
+
+All upload-limit vars are validated (must be a positive integer) and optional; an invalid value fails fast at startup.

 ### Built-in MCP servers (optional setup)

@@ -51,10 +51,10 @@ from starlette.middleware.base import BaseHTTPMiddleware
 # Core imports
 from core.constants import (
    BASE_DIR, STATIC_DIR, SESSIONS_FILE,
-    REQUEST_TIMEOUT, OPENAI_API_KEY,
+    REQUEST_TIMEOUT, OPENAI_API_KEY, AUTH_FILE,
 )
 from core.database import SessionLocal, ApiToken
-from core.middleware import SecurityHeadersMiddleware
+from core.middleware import SecurityHeadersMiddleware, is_cors_preflight
 from core.auth import AuthManager
 from core.exceptions import (
    SessionNotFoundError, InvalidFileUploadError,
@@ -64,6 +64,7 @@ from core.exceptions import (
 import bcrypt as _bcrypt

 from src.app_helpers import abs_join
+from src.generated_images import GENERATED_IMAGE_HEADERS, resolve_generated_image_path
 from starlette.responses import RedirectResponse

 # ========= LOGGING =========
@@ -252,6 +253,15 @@ if AUTH_ENABLED:
    class AuthMiddleware(BaseHTTPMiddleware):
        async def dispatch(self, request: Request, call_next):
            path = request.url.path
+            # A genuine CORS preflight (OPTIONS + Access-Control-Request-Method)
+            # carries no credentials by design and must reach CORSMiddleware to be
+            # answered. AuthMiddleware is the outermost middleware, so gating the
+            # preflight on auth 401s it before CORS can respond -- which blocks
+            # every cross-origin browser/WebView client before the real request
+            # is sent. Let real preflights through (only OPTIONS w/ the ACRM
+            # header; never a credentialed request).
+            if is_cors_preflight(request.method, request.headers):
+                return await call_next(request)
            if _is_auth_exempt(path):
                return await call_next(request)
            # In-process internal-tool token bypass. Used by the agent
@@ -387,13 +397,7 @@ app.mount("/static", _RevalidatingStatic(directory="static"), name="static")
@app.get("/api/generated-image/{filename}")
 async def serve_generated_image(filename: str, request: Request):
    """Serve generated images from the data directory."""
-    from pathlib import Path
-    import re
-    if not re.match(r'^[a-f0-9]{8,64}\.(png|jpg|jpeg|webp|gif|mp4|mov|webm|mkv|m4v)$', filename):
-        raise HTTPException(status_code=400, detail="Invalid filename")
-    img_path = Path("data/generated_images") / filename
-    if not img_path.exists():
-        raise HTTPException(status_code=404, detail="Image not found")
+    img_path = resolve_generated_image_path(filename)
    # SECURITY: filename is the only key, so anyone who knows / guesses a
    # 12-hex content hash could pull another user's image bytes. Require
    # auth and verify ownership via the gallery row (when one exists).
@@ -429,7 +433,7 @@ async def serve_generated_image(filename: str, request: Request):
    return FileResponse(
        str(img_path),
        media_type=mime,
-        headers={"Cache-Control": "public, max-age=31536000, immutable"},
+        headers=GENERATED_IMAGE_HEADERS,
    )

 # ========= YOUTUBE INIT =========
@@ -525,9 +529,6 @@ upload_cleanup_task = None
 from routes.emoji_routes import setup_emoji_routes
 app.include_router(setup_emoji_routes())

-from routes.workspace_routes import setup_workspace_routes
-app.include_router(setup_workspace_routes())
-
 # Sessions
 from routes.session_routes import setup_session_routes
 session_config = {"REQUEST_TIMEOUT": REQUEST_TIMEOUT, "OPENAI_API_KEY": OPENAI_API_KEY, "SESSIONS_FILE": SESSIONS_FILE}
@@ -594,6 +595,10 @@ app.include_router(setup_model_routes(model_discovery))
 from routes.copilot_routes import setup_copilot_routes
 app.include_router(setup_copilot_routes())

+# ChatGPT Subscription device-flow login
+from routes.chatgpt_subscription_routes import setup_chatgpt_subscription_routes
+app.include_router(setup_chatgpt_subscription_routes())
+
 # TTS
 from routes.tts_routes import setup_tts_routes
 app.include_router(setup_tts_routes(tts_service))
@@ -789,6 +794,8 @@ async def serve_backgrounds(request: Request):

@app.get("/login")
 async def serve_login(request: Request):
+    if not AUTH_ENABLED:
+        return RedirectResponse(url="/", status_code=302)
    return _serve_html_with_nonce(request, abs_join(BASE_DIR, "static/login.html"))

@app.get("/api/version")
@@ -948,7 +955,7 @@ async def _startup_event():
        owners = set()
        try:
            import json as _json
-            auth_path = "data/auth.json"
+            auth_path = AUTH_FILE
            with open(auth_path, encoding="utf-8") as f:
                users = _json.load(f).get("users", {})
            owners.update(users.keys())
@@ -995,7 +1002,7 @@ async def _startup_event():
    # does not make an existing library look empty after auth/account changes.
    try:
        import json as _json
-        auth_path = "data/auth.json"
+        auth_path = AUTH_FILE
        with open(auth_path, encoding="utf-8") as f:
            users = _json.load(f).get("users", {})
        primary_owner = None
@@ -1067,6 +1074,16 @@ async def _startup_event():
                logger.warning(f"Nightly skill audit failed: {e}")

    _startup_tasks.append(asyncio.create_task(_skill_audit_nightly_loop()))
+
+    # Cookbook serve lifecycle — kills scheduler-launched serves whose
+    # window-end has passed. Paired with the cookbook_serve builtin
+    # action; both are no-ops unless a scheduled task actually launches
+    # something with end_after_min set. Removing this line + the
+    # cookbook_serve entry in BUILTIN_ACTIONS + src/cookbook_serve_lifecycle.py
+    # removes the feature.
+    from src.cookbook_serve_lifecycle import cookbook_serve_lifecycle_loop
+    _startup_tasks.append(asyncio.create_task(cookbook_serve_lifecycle_loop()))
+
    logger.info("Application startup complete")

 async def _shutdown_event():
@@ -14,6 +14,8 @@ import uuid

 import bcrypt

+from src.constants import AUTH_FILE
+
 PAIRING_VERSION = 1
 COMPANION_SCOPE = "chat"

@@ -61,7 +63,7 @@ def lan_ip_candidates() -> list[str]:
 def find_admin_user() -> str | None:
    """Resolve an admin username from data/auth.json (schema uses is_admin),
    falling back to the first user."""
-    auth_path = os.path.join("data", "auth.json")
+    auth_path = AUTH_FILE
    try:
        with open(auth_path, "r", encoding="utf-8") as f:
            data = json.load(f)
@@ -30,14 +30,24 @@ DEFAULT_PRIVILEGES = {
    "can_manage_memory": True,
    "max_messages_per_day": 0,
    "allowed_models": [],
+    "allowed_models_restricted": False,
+    # Explicit "block every model" sentinel. An empty `allowed_models` list is
+    # ambiguous — it's also what gets sent when the admin clicks "[All]" — so
+    # we need a dedicated flag to express "this user may use no models at all"
+    # distinctly from "this user has no restriction".
+    "block_all_models": False,
 }

 # Admins get everything
 ADMIN_PRIVILEGES = {k: (True if isinstance(v, bool) else (0 if isinstance(v, int) else [])) for k, v in DEFAULT_PRIVILEGES.items()}
+ADMIN_PRIVILEGES["allowed_models_restricted"] = False
+# Admins must never be blocked from using models — the generic dict
+# comprehension above flips every boolean default to True, which would be
+# backwards for this sentinel.
+ADMIN_PRIVILEGES["block_all_models"] = False

-DEFAULT_AUTH_PATH = os.path.join(
-    Path(__file__).parent.parent, "data", "auth.json"
-)
+from src.constants import AUTH_FILE
+DEFAULT_AUTH_PATH = AUTH_FILE
 TOKEN_TTL = 60 * 60 * 24 * 7  # 7 days

 # Usernames the auth + middleware layer reserve as internal "synthetic owner"
@@ -76,6 +86,10 @@ class AuthManager:
        # Guards mutations of self._sessions and the on-disk sessions.json.
        # Validate/create/revoke run concurrently from the FastAPI threadpool.
        self._sessions_lock = threading.RLock()
+        # Guards all mutations of self._config and the on-disk auth.json so
+        # concurrent create/delete/rename/privilege operations don't interleave
+        # and corrupt the user database.
+        self._config_lock = threading.Lock()
        # Guards the first-run setup check-and-write so concurrent requests
        # cannot both observe is_configured==False and both create admin accounts.
        self._setup_lock = threading.Lock()
@@ -172,8 +186,9 @@ class AuthManager:

    @signup_enabled.setter
    def signup_enabled(self, value: bool):
-        self._config["signup_enabled"] = value
-        self._save()
+        with self._config_lock:
+            self._config["signup_enabled"] = value
+            self._save()

    @property
    def is_configured(self) -> bool:
@@ -198,17 +213,18 @@ class AuthManager:
        if username in RESERVED_USERNAMES:
            logger.warning("Refused to create reserved username '%s'", username)
            return False
-        if username in self.users:
-            return False
-        if "users" not in self._config:
-            self._config["users"] = {}
-        self._config["users"][username] = {
-            "password_hash": _hash_password(password),
-            "created": time.time(),
-            "is_admin": is_admin,
-            "privileges": dict(ADMIN_PRIVILEGES if is_admin else DEFAULT_PRIVILEGES),
-        }
-        self._save()
+        with self._config_lock:
+            if username in self.users:
+                return False
+            if "users" not in self._config:
+                self._config["users"] = {}
+            self._config["users"][username] = {
+                "password_hash": _hash_password(password),
+                "created": time.time(),
+                "is_admin": is_admin,
+                "privileges": dict(ADMIN_PRIVILEGES if is_admin else DEFAULT_PRIVILEGES),
+            }
+            self._save()
        logger.info(f"Created user '{username}' (admin={is_admin})")
        return True

@@ -221,14 +237,15 @@ class AuthManager:
        their cookie expired naturally (default ~30 days).
        """
        username = username.strip().lower()
-        if username not in self.users:
-            return False
-        if username == requesting_user:
-            return False
-        if not self.users.get(requesting_user, {}).get("is_admin"):
-            return False
-        del self._config["users"][username]
-        self._save()
+        with self._config_lock:
+            if username not in self.users:
+                return False
+            if username == requesting_user:
+                return False
+            if not self.users.get(requesting_user, {}).get("is_admin"):
+                return False
+            del self._config["users"][username]
+            self._save()
        # Purge all sessions belonging to this user. validate_token doesn't
        # cross-check `self.users`, so without this step a deleted user's
        # cookie keeps authenticating.
@@ -266,14 +283,15 @@ class AuthManager:
        if new_username in RESERVED_USERNAMES:
            logger.warning("Refused to rename '%s' into reserved username '%s'", old_username, new_username)
            return False
-        if old_username not in self.users:
-            return False
-        if new_username in self.users:
-            return False
-        if not self.users.get(requesting_user, {}).get("is_admin"):
-            return False
-        self._config.setdefault("users", {})[new_username] = self._config["users"].pop(old_username)
-        self._save()
+        with self._config_lock:
+            if old_username not in self.users:
+                return False
+            if new_username in self.users:
+                return False
+            if not self.users.get(requesting_user, {}).get("is_admin"):
+                return False
+            self._config.setdefault("users", {})[new_username] = self._config["users"].pop(old_username)
+            self._save()

        renamed_sessions = 0
        with self._sessions_lock:
@@ -311,17 +329,18 @@ class AuthManager:
    def set_privileges(self, username: str, privileges: Dict[str, Any]) -> bool:
        """Update privileges for a user. Can't modify admin privileges."""
        username = username.strip().lower()
-        if username not in self.users:
-            return False
-        if self.users[username].get("is_admin"):
-            return False  # admins always have full access
-        # Only allow known privilege keys
-        current = self.get_privileges(username)
-        for k, v in privileges.items():
-            if k in DEFAULT_PRIVILEGES:
-                current[k] = v
-        self._config["users"][username]["privileges"] = current
-        self._save()
+        with self._config_lock:
+            if username not in self.users:
+                return False
+            if self.users[username].get("is_admin"):
+                return False  # admins always have full access
+            # Only allow known privilege keys
+            current = self.get_privileges(username)
+            for k, v in privileges.items():
+                if k in DEFAULT_PRIVILEGES:
+                    current[k] = v
+            self._config["users"][username]["privileges"] = current
+            self._save()
        logger.info(f"Updated privileges for '{username}': {current}")
        return True

@@ -331,8 +350,9 @@ class AuthManager:
            return False
        if not _verify_password(current_password, self.users[username]["password_hash"]):
            return False
-        self._config["users"][username]["password_hash"] = _hash_password(new_password)
-        self._save()
+        with self._config_lock:
+            self._config["users"][username]["password_hash"] = _hash_password(new_password)
+            self._save()
        return True

    # ------------------------------------------------------------------
@@ -350,8 +370,9 @@ class AuthManager:
        if username not in self.users:
            return None
        secret = pyotp.random_base32()
-        self._config["users"][username]["totp_secret_pending"] = secret
-        self._save()
+        with self._config_lock:
+            self._config["users"][username]["totp_secret_pending"] = secret
+            self._save()
        return secret

    def totp_get_provisioning_uri(self, username: str, secret: str) -> str:
@@ -370,13 +391,14 @@ class AuthManager:
        if not totp.verify(code, valid_window=1):
            return False
        # Enable 2FA
-        self._config["users"][username]["totp_secret"] = secret
-        self._config["users"][username]["totp_enabled"] = True
-        self._config["users"][username].pop("totp_secret_pending", None)
-        # Generate backup codes
-        backup = [secrets.token_hex(4) for _ in range(8)]
-        self._config["users"][username]["totp_backup_codes"] = backup
-        self._save()
+        with self._config_lock:
+            self._config["users"][username]["totp_secret"] = secret
+            self._config["users"][username]["totp_enabled"] = True
+            self._config["users"][username].pop("totp_secret_pending", None)
+            # Generate backup codes
+            backup = [secrets.token_hex(4) for _ in range(8)]
+            self._config["users"][username]["totp_backup_codes"] = backup
+            self._save()
        logger.info(f"2FA enabled for '{username}'")
        return True

@@ -395,9 +417,10 @@ class AuthManager:
        # Check backup codes first
        backup = user.get("totp_backup_codes", [])
        if code in backup:
-            backup.remove(code)
-            self._config["users"][username]["totp_backup_codes"] = backup
-            self._save()
+            with self._config_lock:
+                backup.remove(code)
+                self._config["users"][username]["totp_backup_codes"] = backup
+                self._save()
            logger.info(f"Backup code used for '{username}' ({len(backup)} remaining)")
            return True
        totp = pyotp.TOTP(secret)
@@ -408,11 +431,12 @@ class AuthManager:
        username = username.strip().lower()
        if not self.verify_password(username, password):
            return False
-        self._config["users"][username].pop("totp_secret", None)
-        self._config["users"][username].pop("totp_secret_pending", None)
-        self._config["users"][username].pop("totp_backup_codes", None)
-        self._config["users"][username]["totp_enabled"] = False
-        self._save()
+        with self._config_lock:
+            self._config["users"][username].pop("totp_secret", None)
+            self._config["users"][username].pop("totp_secret_pending", None)
+            self._config["users"][username].pop("totp_backup_codes", None)
+            self._config["users"][username]["totp_enabled"] = False
+            self._save()
        logger.info(f"2FA disabled for '{username}'")
        return True

@@ -431,6 +455,12 @@ class AuthManager:
        username = username.strip().lower()
        if not self.verify_password(username, password):
            return None
+        return self.create_session_trusted(username)
+
+    def create_session_trusted(self, username: str) -> str:
+        """Issue a session token for an already-verified user.
+        Call only after verify_password (and TOTP if enabled) have passed."""
+        username = username.strip().lower()
        token = secrets.token_hex(32)
        with self._sessions_lock:
            self._sessions[token] = {
@@ -1,40 +1,12 @@
-# src/constants.py
-"""Application-wide constants and configuration values."""
-import os
+# core/constants.py
+"""Backward-compatible shim — the single source of truth is src/constants.py.

-APP_VERSION = "0.9.1"
-
-# Base paths
-BASE_DIR = os.path.dirname(os.path.dirname(os.path.abspath(__file__))) + "/"
-STATIC_DIR = os.path.join(BASE_DIR, "static")
-DATA_DIR = os.path.join(BASE_DIR, "data")
-
-# Data file paths
-SESSIONS_FILE = os.path.join(DATA_DIR, "sessions.json")
-MEMORY_FILE = os.path.join(DATA_DIR, "memory.json")
-MEMORY_DOC = os.path.join(DATA_DIR, "memory_doc.md")
-PERSONAL_DIR = os.path.join(DATA_DIR, "personal_docs")
-RUNBOOK_DIR = os.path.join(PERSONAL_DIR, "runbook")
-UPLOAD_DIR = os.path.join(DATA_DIR, "uploads")
-FEATURES_FILE = os.path.join(DATA_DIR, "features.json")
-SETTINGS_FILE = os.path.join(DATA_DIR, "settings.json")
-
-# API Configuration
-MAX_CONTEXT_MESSAGES = 90
-REQUEST_TIMEOUT = 20
-OPENAI_COMPAT_PATH = "/v1/chat/completions"
-
-# Environment variables with defaults
-DEFAULT_HOST = os.getenv("LLM_HOST", "localhost")
-LLM_HOSTS = [h.strip() for h in os.getenv("LLM_HOSTS", "").split(",") if h.strip()]
-OPENAI_API_KEY = os.getenv("OPENAI_API_KEY")
-SEARXNG_INSTANCE = os.getenv('SEARXNG_INSTANCE', 'http://localhost:8080')
-
-
-# Cleanup configuration
-CLEANUP_ENABLED = os.getenv("CLEANUP_ENABLED", "True").lower() == "true"
-CLEANUP_INTERVAL_HOURS = int(os.getenv("CLEANUP_INTERVAL_HOURS", "24"))
-
-# Default parameters
-DEFAULT_TEMPERATURE = 1.0
-DEFAULT_MAX_TOKENS = 0
+Historically there were two copies of this module (this one lagged behind at
+APP_VERSION 0.9.1 and was missing the consolidated tool-output constants). To
+kill the drift, this now simply re-exports everything from src.constants so
+there is exactly one place that defines paths and reads ODYSSEUS_DATA_DIR.
+internal_api_base() also lives in src.constants now and is re-exported here so
+existing `from core.constants import internal_api_base` callers keep working.
+"""
+from src.constants import *  # noqa: F401,F403
+from src.constants import internal_api_base  # noqa: F401  (explicit: functions aren't covered by some linters' * checks)
@@ -29,8 +29,9 @@ class TimestampMixin:
    def updated_at(cls):
        return Column(DateTime, default=utcnow_naive, onupdate=utcnow_naive, nullable=False)

-# Get database URL from environment, default to SQLite
-DATABASE_URL = os.getenv("DATABASE_URL", "sqlite:///./data/app.db")
+# Get database URL from environment, default to SQLite in DATA_DIR
+from src.constants import DATA_DIR, AUTH_FILE, MEMORY_FILE, USER_PREFS_FILE, SETTINGS_FILE
+DATABASE_URL = os.getenv("DATABASE_URL", f"sqlite:///{DATA_DIR}/app.db")

 # Create engine
 engine = create_engine(
@@ -360,6 +361,24 @@ class ModelEndpoint(TimestampMixin, Base):
    # is the historical default. When non-null, the model picker only shows
    # the endpoint to that user (admins always see everything).
    owner = Column(String, nullable=True, index=True)
+    # Optional OAuth/session-backed credential row. Used by subscription-backed
+    # providers that need refresh tokens instead of a static API key.
+    provider_auth_id = Column(String, nullable=True, index=True)
+
+
+class ProviderAuthSession(TimestampMixin, Base):
+    """Encrypted OAuth/session credentials for refresh-aware model providers."""
+    __tablename__ = "provider_auth_sessions"
+
+    id = Column(String, primary_key=True, index=True)
+    provider = Column(String, nullable=False, index=True)
+    owner = Column(String, nullable=True, index=True)
+    label = Column(String, nullable=True)
+    base_url = Column(String, nullable=False)
+    access_token = Column(EncryptedText, nullable=True)
+    refresh_token = Column(EncryptedText, nullable=True)
+    last_refresh = Column(DateTime, nullable=True)
+    auth_mode = Column(String, nullable=True)

 class McpServer(TimestampMixin, Base):
    """Admin-configured MCP (Model Context Protocol) tool servers."""
@@ -800,6 +819,26 @@ def _migrate_add_model_endpoint_owner_column():
        logging.getLogger(__name__).warning(f"model_endpoints.owner migration failed: {e}")


+def _migrate_add_provider_auth_id_column():
+    """Add provider_auth_id column to model_endpoints if it doesn't exist."""
+    import sqlite3
+    db_path = DATABASE_URL.replace("sqlite:///", "")
+    if not os.path.exists(db_path):
+        return
+    try:
+        conn = sqlite3.connect(db_path)
+        cursor = conn.execute("PRAGMA table_info(model_endpoints)")
+        columns = [row[1] for row in cursor.fetchall()]
+        if columns and "provider_auth_id" not in columns:
+            conn.execute("ALTER TABLE model_endpoints ADD COLUMN provider_auth_id VARCHAR")
+            conn.execute("CREATE INDEX IF NOT EXISTS ix_model_endpoints_provider_auth_id ON model_endpoints(provider_auth_id)")
+            conn.commit()
+            logging.getLogger(__name__).info("Migrated: added 'provider_auth_id' column + index to model_endpoints")
+        conn.close()
+    except Exception as e:
+        logging.getLogger(__name__).warning(f"model_endpoints.provider_auth_id migration failed: {e}")
+
+
 def _migrate_add_model_type_column():
    """Add model_type column to model_endpoints if it doesn't exist."""
    import sqlite3
@@ -1065,7 +1104,7 @@ def _migrate_assign_legacy_owner():
    # fell through to "first user" every time.
    auth_path = os.path.join(os.path.dirname(DATABASE_URL.replace("sqlite:///", "")), "auth.json")
    if not os.path.isabs(auth_path):
-        auth_path = os.path.join("data", "auth.json")
+        auth_path = AUTH_FILE
    admin_user = None
    try:
        with open(auth_path, "r", encoding="utf-8") as f:
@@ -1118,7 +1157,7 @@ def _migrate_assign_legacy_owner():
        logger.warning(f"Legacy owner migration failed: {e}")

    # Also migrate memory.json
-    mem_path = os.path.join("data", "memory.json")
+    mem_path = MEMORY_FILE
    try:
        if os.path.exists(mem_path):
            with open(mem_path, "r", encoding="utf-8") as f:
@@ -1136,7 +1175,7 @@ def _migrate_assign_legacy_owner():
        logger.warning(f"memory.json legacy migration failed: {e}")

    # Also migrate user_prefs.json to per-user format
-    prefs_path = os.path.join("data", "user_prefs.json")
+    prefs_path = USER_PREFS_FILE
    try:
        if os.path.exists(prefs_path):
            with open(prefs_path, "r", encoding="utf-8") as f:
@@ -1458,7 +1497,11 @@ class CalendarCal(TimestampMixin, Base):
    owner = Column(String, nullable=True, index=True)
    name  = Column(String, nullable=False)
    color = Column(String, default="#5b8abf")
-    source = Column(String, default="local")  # "local" or "timetree"
+    source = Column(String, default="local")  # "local" or "caldav"
+    # UUID of the CalDAV account in user prefs that owns this calendar.
+    # NULL for local calendars and for CalDAV calendars created before
+    # multi-account support was added (treated as "use any configured account").
+    account_id = Column(String, nullable=True, index=True)

    events = relationship("CalendarEvent", back_populates="calendar", cascade="all, delete-orphan")

@@ -1526,7 +1569,7 @@ def _migrate_seed_email_account():
        import json as _json
        import uuid as _uuid
        from pathlib import Path
-        settings_file = Path("data/settings.json")
+        settings_file = Path(SETTINGS_FILE)
        if not settings_file.exists():
            return
        try:
@@ -1594,6 +1637,7 @@ def init_db():
    _migrate_add_model_type_column()
    _migrate_add_model_endpoint_refresh_columns()
    _migrate_add_model_endpoint_owner_column()
+    _migrate_add_provider_auth_id_column()
    _migrate_add_supports_tools_column()
    _migrate_add_task_run_model_column()
    _migrate_add_owner_column()
@@ -1622,9 +1666,105 @@ def init_db():
    _migrate_add_calendar_metadata()
    _migrate_add_calendar_is_utc()
    _migrate_add_calendar_origin()
+    _migrate_add_calendar_account_id()
+    _migrate_chat_messages_fts()
    _migrate_encrypt_email_passwords()
    _migrate_encrypt_signatures()
    _migrate_encrypt_endpoint_keys()
+    _migrate_backfill_task_folders()
+
+
+def _migrate_backfill_task_folders():
+    """Backfill folder='Tasks' on pre-existing task/research sessions.
+
+    Sessions created by the task scheduler (LLM tasks, action tasks, research
+    runs) now set folder='Tasks' at creation time.  This migration tags any
+    older sessions that predate that assignment.  Idempotent — only touches
+    rows where folder is NULL or empty and the title matches known prefixes.
+    """
+    try:
+        with engine.connect() as conn:
+            cols = [r[1] for r in conn.execute(text("PRAGMA table_info(sessions)"))]
+            if "folder" not in cols:
+                return
+            res = conn.execute(text(
+                "UPDATE sessions SET folder = 'Tasks' "
+                "WHERE (folder IS NULL OR folder = '') "
+                "AND (name LIKE '[Task] %' OR name LIKE '[Research] %')"
+            ))
+            conn.commit()
+            if res.rowcount:
+                logging.getLogger(__name__).info(
+                    f"Backfilled folder='Tasks' on {res.rowcount} task/research sessions")
+    except Exception as e:
+        logging.getLogger(__name__).warning(f"task folder backfill: {e}")
+
+
+def _migrate_chat_messages_fts():
+    """Create and backfill the session transcript FTS index for SQLite."""
+    if not DATABASE_URL.startswith("sqlite"):
+        return
+
+    db_path = DATABASE_URL.replace("sqlite:///", "")
+    if db_path == ":memory:":
+        return
+    conn = None
+    try:
+        conn = sqlite3.connect(db_path)
+        try:
+            conn.execute("CREATE VIRTUAL TABLE IF NOT EXISTS temp._odysseus_fts5_probe USING fts5(content)")
+            conn.execute("DROP TABLE IF EXISTS temp._odysseus_fts5_probe")
+        except Exception as e:
+            logging.getLogger(__name__).warning(f"chat_messages FTS migration skipped; FTS5 unavailable: {e}")
+            return
+
+        conn.executescript(
+            """
+            CREATE VIRTUAL TABLE IF NOT EXISTS chat_messages_fts USING fts5(
+                content,
+                message_id UNINDEXED,
+                session_id UNINDEXED,
+                role UNINDEXED
+            );
+
+            CREATE TRIGGER IF NOT EXISTS chat_messages_fts_ai
+            AFTER INSERT ON chat_messages BEGIN
+                INSERT INTO chat_messages_fts(content, message_id, session_id, role)
+                VALUES (COALESCE(new.content, ''), new.id, new.session_id, new.role);
+            END;
+
+            CREATE TRIGGER IF NOT EXISTS chat_messages_fts_ad
+            AFTER DELETE ON chat_messages BEGIN
+                DELETE FROM chat_messages_fts WHERE message_id = old.id;
+            END;
+
+            CREATE TRIGGER IF NOT EXISTS chat_messages_fts_au
+            AFTER UPDATE ON chat_messages BEGIN
+                DELETE FROM chat_messages_fts WHERE message_id = old.id;
+                INSERT INTO chat_messages_fts(content, message_id, session_id, role)
+                VALUES (COALESCE(new.content, ''), new.id, new.session_id, new.role);
+            END;
+            """
+        )
+        conn.execute(
+            """
+            INSERT INTO chat_messages_fts(content, message_id, session_id, role)
+            SELECT COALESCE(cm.content, ''), cm.id, cm.session_id, cm.role
+            FROM chat_messages cm
+            WHERE NOT EXISTS (
+                SELECT 1 FROM chat_messages_fts fts
+                WHERE fts.message_id = cm.id
+            )
+            """
+        )
+        conn.commit()
+    except Exception as e:
+        logging.getLogger(__name__).warning(f"chat_messages FTS migration failed: {e}")
+    finally:
+        try:
+            conn.close()
+        except Exception:
+            pass


 def _migrate_add_email_smtp_security():
@@ -1786,6 +1926,27 @@ def _migrate_add_calendar_origin():
        logging.getLogger(__name__).warning(f"calendar_events.origin migration failed: {e}")


+def _migrate_add_calendar_account_id():
+    """Add `account_id` to calendars so each CalDAV-backed calendar knows which
+    credential set (from caldav_accounts in user prefs) owns it. Idempotent."""
+    import sqlite3
+    db_path = DATABASE_URL.replace("sqlite:///", "")
+    if not os.path.exists(db_path):
+        return
+    try:
+        conn = sqlite3.connect(db_path)
+        cursor = conn.execute("PRAGMA table_info(calendars)")
+        columns = [row[1] for row in cursor.fetchall()]
+        if columns and "account_id" not in columns:
+            conn.execute("ALTER TABLE calendars ADD COLUMN account_id TEXT")
+            conn.execute("CREATE INDEX IF NOT EXISTS ix_calendars_account_id ON calendars(account_id)")
+            conn.commit()
+            logging.getLogger(__name__).info("Migrated: added 'account_id' column to calendars")
+        conn.close()
+    except Exception as e:
+        logging.getLogger(__name__).warning(f"calendars.account_id migration failed: {e}")
+
+
 def _migrate_add_calendar_metadata():
    """Add importance/event_type/last_pinged columns to calendar_events table."""
    import sqlite3
@@ -17,6 +17,15 @@ INTERNAL_TOOL_TOKEN = os.environ.get("ODYSSEUS_INTERNAL_TOKEN") or secrets.token
 INTERNAL_TOOL_HEADER = "X-Odysseus-Internal-Token"


+def is_cors_preflight(method: str, headers) -> bool:
+    """True for a genuine CORS preflight: an OPTIONS request carrying the
+    Access-Control-Request-Method header. Such requests are credential-less by
+    design and must reach CORSMiddleware to be answered -- gating them on auth
+    401s the preflight and breaks every cross-origin browser/WebView client.
+    Pure so it can be unit-tested without standing up the app."""
+    return method == "OPTIONS" and "access-control-request-method" in headers
+
+
 def require_admin(request: Request):
    """Raise 403 if the current user isn't an admin.
    Allows access when auth is explicitly disabled, or when the request carries
@@ -58,11 +67,22 @@ class SecurityHeadersMiddleware(BaseHTTPMiddleware):

        # Tool render endpoints are served inside iframes — allow framing by self
        is_tool_render = path.startswith("/api/tools/") and path.endswith("/render")
+        # PDF previews are embedded by the in-app document library. Keep the
+        # exception route-scoped so normal app pages remain unframeable.
+        is_document_pdf_preview = path.startswith("/api/document/") and path.endswith("/render-pdf")
        # Visual report pages are self-contained HTML — need inline scripts + external images
        is_report = path.startswith("/api/research/report/")

        response.headers["X-Content-Type-Options"] = "nosniff"
        response.headers["Referrer-Policy"] = "no-referrer"
+        response.headers["Permissions-Policy"] = "camera=(), microphone=(self), geolocation=()"
+
+        is_https = (
+            request.url.scheme == "https"
+            or request.headers.get("X-Forwarded-Proto") == "https"
+        )
+        if is_https:
+            response.headers["Strict-Transport-Security"] = "max-age=31536000; includeSubDomains"

        if is_report:
            response.headers["Content-Security-Policy"] = (
@@ -79,6 +99,12 @@ class SecurityHeadersMiddleware(BaseHTTPMiddleware):
            # sandbox="allow-scripts" attribute provides isolation.
            # Don't overwrite the route's own restrictive CSP either.
            pass
+        elif is_document_pdf_preview:
+            response.headers["X-Frame-Options"] = "SAMEORIGIN"
+            response.headers["Content-Security-Policy"] = (
+                "default-src 'none'; "
+                "frame-ancestors 'self'"
+            )
        else:
            response.headers["X-Frame-Options"] = "DENY"
            # NOTE: `style-src 'unsafe-inline'` is intentionally retained.
@@ -18,10 +18,22 @@ import ntpath
 import shutil
 import subprocess
 from pathlib import Path
+import sys
 from typing import List, Optional
+import platform

 IS_WINDOWS = os.name == "nt"
 IS_POSIX = not IS_WINDOWS
+# Allows APFEL support and ARM-native binary recommendations on Apple Silicon Macs.
+IS_APPLE_SILICON = (
+    IS_POSIX
+    and platform.system() == "Darwin"
+    and platform.machine().lower()
+    in {
+        "arm64",
+        "aarch64",
+    }
+)


 # ── File permissions ────────────────────────────────────────────────────────
@@ -53,9 +65,8 @@ def detached_popen_kwargs() -> dict:
    and is detached from any console.
    """
    if IS_WINDOWS:
-        flags = (
-            getattr(subprocess, "CREATE_NEW_PROCESS_GROUP", 0x00000200)
-            | getattr(subprocess, "DETACHED_PROCESS", 0x00000008)
+        flags = getattr(subprocess, "CREATE_NEW_PROCESS_GROUP", 0x00000200) | getattr(
+            subprocess, "DETACHED_PROCESS", 0x00000008
        )
        return {"creationflags": flags}
    return {"start_new_session": True}
@@ -150,6 +161,29 @@ _WINDOWS_BASH_RELATIVE_PATHS = (
    ("usr", "bin", "bash.exe"),
 )

+# Paths to add to the remote SSH probe command to find tools like nvidia-smi that may not be on PATH.
+_SSH_PATH_MEMBERS = (
+    "/usr/bin",
+    "/usr/local/bin",
+    "/usr/local/cuda/bin",
+    "/usr/lib/wsl/lib"
+)
+# Fallback locations for nvidia-smi on WSL and other Linux distros where it may not be on PATH.
+NVIDIA_PATH_CANDIDATES = (
+    "/usr/bin/nvidia-smi",
+    "/usr/local/bin/nvidia-smi",
+    "/usr/local/cuda/bin/nvidia-smi",
+    "/usr/lib/wsl/lib/nvidia-smi",
+)
+
+
+def _ssh_path_override() -> str:
+    """Build the PATH export snippet used for remote SSH shell probes."""
+    return f"export PATH=\"$PATH:{':'.join(_SSH_PATH_MEMBERS)}\"; "
+
+
+SSH_PATH_OVERRIDE = _ssh_path_override()
+

 def _windows_bash_fallbacks() -> List[str]:
    roots: List[str] = []
@@ -180,6 +214,21 @@ def _is_windows_bash_stub(path: str) -> bool:
    )


+def git_bash_path(path: str | Path) -> str:
+    """Convert a path to POSIX style suitable for Git Bash on Windows.
+
+    Transforms drive letters (e.g., 'C:\\path') to POSIX '/c/path',
+    and uses forward slashes.
+    """
+    p = Path(path)
+    p_str = p.as_posix()
+    if IS_WINDOWS and len(p_str) >= 2 and p_str[1] == ":":
+        drive = p_str[0].lower()
+        return f"/{drive}{p_str[2:]}"
+    return p_str
+
+
+
 def find_bash() -> Optional[str]:
    """Locate a real ``bash`` interpreter, or None.

@@ -242,3 +291,156 @@ def run_script_argv(script_path) -> List[str]:
        comspec = os.environ.get("ComSpec", "cmd.exe")
        return [comspec, "/c", str(script_path)]
    return ["sh", str(script_path)]
+
+
+def is_wsl() -> bool:
+    """True if running inside Windows Subsystem for Linux (WSL)."""
+    import sys
+    if sys.platform.startswith("linux") or os.name == "posix":
+        try:
+            with open("/proc/version", "r") as f:
+                if "microsoft" in f.read().lower():
+                    return True
+        except Exception:
+            pass
+    return False
+
+
+def translate_path(path_str: str) -> str:
+    """Translate a path (possibly a Windows path) to the current OS format.
+
+    Particularly handles Windows paths (e.g. C:\\foo or C:/foo) when running
+    under WSL, translating them to /mnt/c/foo.
+    Also handles standard path normalization to avoid string breakages.
+    """
+    if not path_str:
+        return path_str
+
+    if is_wsl():
+        path_str = path_str.replace("\\", "/")
+        import re
+        m = re.match(r"^([a-zA-Z]):(.*)", path_str)
+        if m:
+            drive = m.group(1).lower()
+            rest = m.group(2)
+            if not rest.startswith("/"):
+                rest = "/" + rest
+            return f"/mnt/{drive}{rest}"
+
+    try:
+        return str(Path(path_str).resolve())
+    except Exception:
+        return path_str
+
+
+def get_wsl_windows_user_profile() -> Optional[str]:
+    """Retrieve the Windows host User Profile path from inside WSL."""
+    if not is_wsl():
+        return None
+    try:
+        r = run_wsl_windows_powershell("Write-Output $env:USERPROFILE", timeout=5)
+        if r.returncode == 0 and r.stdout.strip():
+            return translate_path(r.stdout.strip())
+    except Exception:
+        pass
+
+    try:
+        users_dir = "/mnt/c/Users"
+        if os.path.isdir(users_dir):
+            for entry in os.listdir(users_dir):
+                if entry not in ("All Users", "Default", "Default User", "desktop.ini", "Public"):
+                    path = os.path.join(users_dir, entry)
+                    if os.path.isdir(path):
+                        return path
+    except Exception:
+        pass
+    return None
+
+
+def _ssh_exec_argv(
+    remote: str,
+    ssh_port: str | None,
+    *,
+    remote_cmd: str | None = None,
+    connect_timeout: int | None = None,
+    strict_host_key_checking: bool | None = None,
+) -> list[str]:
+    """Build a consistent ssh argv for remote command execution."""
+    argv = ["ssh"]
+    if connect_timeout is not None:
+        argv.extend(["-o", f"ConnectTimeout={int(connect_timeout)}"])
+    if strict_host_key_checking is not None:
+        argv.extend(
+            [
+                "-o",
+                "StrictHostKeyChecking=yes"
+                if strict_host_key_checking
+                else "StrictHostKeyChecking=no",
+            ]
+        )
+    if ssh_port and ssh_port != "22":
+        argv.extend(["-p", str(ssh_port)])
+    argv.append(remote)
+    if remote_cmd is not None:
+        argv.append(remote_cmd)
+    return argv
+
+
+def run_ssh_command(
+    remote: str,
+    ssh_port: str | None,
+    remote_cmd: str,
+    *,
+    timeout: float,
+    connect_timeout: int | None = None,
+    strict_host_key_checking: bool | None = None,
+    text: bool = True,
+) -> subprocess.CompletedProcess:
+    """Run an ssh command with centralized timeout and stderr/stdout capture."""
+    return subprocess.run(
+        _ssh_exec_argv(
+            remote,
+            ssh_port,
+            remote_cmd=remote_cmd,
+            connect_timeout=connect_timeout,
+            strict_host_key_checking=strict_host_key_checking,
+        ),
+        timeout=timeout,
+        capture_output=True,
+        text=text,
+    )
+
+
+def _windows_powershell_argv(
+    command: str,
+    *,
+    no_profile: bool = True,
+    non_interactive: bool = True,
+) -> List[str]:
+    argv: List[str] = ["powershell.exe"]
+    if no_profile:
+        argv.append("-NoProfile")
+    if non_interactive:
+        argv.append("-NonInteractive")
+    argv.extend(["-Command", command])
+    return argv
+
+
+def run_wsl_windows_powershell(
+    command: str,
+    *,
+    timeout: float = 5,
+) -> subprocess.CompletedProcess[str]:
+    """Run a PowerShell command on the Windows host from WSL.
+
+    Raises ``RuntimeError`` when called outside WSL.
+    """
+
+    if not is_wsl():
+        raise RuntimeError("run_wsl_windows_powershell is only supported in WSL")
+    return subprocess.run(
+        _windows_powershell_argv(command),
+        capture_output=True,
+        text=True,
+        timeout=timeout,
+    )
@@ -14,7 +14,7 @@ import logging
 from datetime import datetime, timezone, timedelta
 from typing import Dict, Optional

-from .database import Session as DbSession, ChatMessage as DbChatMessage, Document as DbDocument, SessionLocal
+from .database import Session as DbSession, ChatMessage as DbChatMessage, Document as DbDocument, SessionLocal, utcnow_naive
 from .models import Session, ChatMessage

 logger = logging.getLogger(__name__)
@@ -619,7 +619,7 @@ class SessionManager:

        try:
            all_sessions = db.query(DbSession).all()
-            cutoff_date = datetime.now(timezone.utc) - timedelta(days=auto_archive_days)
+            cutoff_date = utcnow_naive() - timedelta(days=auto_archive_days)

            for db_session in all_sessions:
                stats['total_checked'] += 1
@@ -52,12 +52,14 @@ services:
      - SECURE_COOKIES=${SECURE_COOKIES:-false}
      - EMBEDDING_URL=${EMBEDDING_URL:-}
      - EMBEDDING_MODEL=${EMBEDDING_MODEL:-}
+      - EMBEDDING_API_KEY=${EMBEDDING_API_KEY:-}
      - FASTEMBED_MODEL=${FASTEMBED_MODEL:-sentence-transformers/all-MiniLM-L6-v2}
      - FASTEMBED_CACHE_PATH=${FASTEMBED_CACHE_PATH:-}
      - CLEANUP_INTERVAL_HOURS=${CLEANUP_INTERVAL_HOURS:-24}
      - ODYSSEUS_INPROCESS_POLLERS=${ODYSSEUS_INPROCESS_POLLERS:-1}
      - ODYSSEUS_INPROCESS_TASKS=${ODYSSEUS_INPROCESS_TASKS:-1}
      - ODYSSEUS_SCRIPT_HOST=${ODYSSEUS_SCRIPT_HOST:-localhost}
+      - ODYSSEUS_CHAT_UPLOAD_MAX_BYTES=${ODYSSEUS_CHAT_UPLOAD_MAX_BYTES:-10485760}
      - DATA_BRAVE_API_KEY=${DATA_BRAVE_API_KEY:-}
      - GOOGLE_API_KEY=${GOOGLE_API_KEY:-}
      - GOOGLE_PSE_CX=${GOOGLE_PSE_CX:-}
@@ -51,12 +51,14 @@ services:
      - SECURE_COOKIES=${SECURE_COOKIES:-false}
      - EMBEDDING_URL=${EMBEDDING_URL:-}
      - EMBEDDING_MODEL=${EMBEDDING_MODEL:-}
+      - EMBEDDING_API_KEY=${EMBEDDING_API_KEY:-}
      - FASTEMBED_MODEL=${FASTEMBED_MODEL:-sentence-transformers/all-MiniLM-L6-v2}
      - FASTEMBED_CACHE_PATH=${FASTEMBED_CACHE_PATH:-}
      - CLEANUP_INTERVAL_HOURS=${CLEANUP_INTERVAL_HOURS:-24}
      - ODYSSEUS_INPROCESS_POLLERS=${ODYSSEUS_INPROCESS_POLLERS:-1}
      - ODYSSEUS_INPROCESS_TASKS=${ODYSSEUS_INPROCESS_TASKS:-1}
      - ODYSSEUS_SCRIPT_HOST=${ODYSSEUS_SCRIPT_HOST:-localhost}
+      - ODYSSEUS_CHAT_UPLOAD_MAX_BYTES=${ODYSSEUS_CHAT_UPLOAD_MAX_BYTES:-10485760}
      - DATA_BRAVE_API_KEY=${DATA_BRAVE_API_KEY:-}
      - GOOGLE_API_KEY=${GOOGLE_API_KEY:-}
      - GOOGLE_PSE_CX=${GOOGLE_PSE_CX:-}
@@ -40,12 +40,14 @@ services:
      - SECURE_COOKIES=${SECURE_COOKIES:-false}
      - EMBEDDING_URL=${EMBEDDING_URL:-}
      - EMBEDDING_MODEL=${EMBEDDING_MODEL:-}
+      - EMBEDDING_API_KEY=${EMBEDDING_API_KEY:-}
      - FASTEMBED_MODEL=${FASTEMBED_MODEL:-sentence-transformers/all-MiniLM-L6-v2}
      - FASTEMBED_CACHE_PATH=${FASTEMBED_CACHE_PATH:-}
      - CLEANUP_INTERVAL_HOURS=${CLEANUP_INTERVAL_HOURS:-24}
      - ODYSSEUS_INPROCESS_POLLERS=${ODYSSEUS_INPROCESS_POLLERS:-1}
      - ODYSSEUS_INPROCESS_TASKS=${ODYSSEUS_INPROCESS_TASKS:-1}
      - ODYSSEUS_SCRIPT_HOST=${ODYSSEUS_SCRIPT_HOST:-localhost}
+      - ODYSSEUS_CHAT_UPLOAD_MAX_BYTES=${ODYSSEUS_CHAT_UPLOAD_MAX_BYTES:-10485760}
      - DATA_BRAVE_API_KEY=${DATA_BRAVE_API_KEY:-}
      - GOOGLE_API_KEY=${GOOGLE_API_KEY:-}
      - GOOGLE_PSE_CX=${GOOGLE_PSE_CX:-}
@@ -0,0 +1,17 @@
+# Outlook / Office 365 email accounts
+
+Odysseus email accounts currently use IMAP and SMTP with username/password
+authentication. That works for providers that still allow app passwords or
+mailbox passwords for IMAP/SMTP.
+
+Microsoft disables basic authentication for Outlook and Microsoft 365 in most
+modern accounts and tenants. If you try to add an Outlook account with a normal
+password, Microsoft may return errors such as:
+
+- `IMAP: AUTHENTICATE failed`
+- `SMTP: 535 5.7.139 Authentication unsuccessful, basic authentication is disabled`
+
+This is expected. Odysseus does not support Microsoft OAuth or Graph Mail yet,
+so Outlook / Office 365 accounts cannot currently be added through the password
+form. Use another email provider with app-password support, or track the future
+Microsoft Graph OAuth integration.
@@ -1,6 +1,6 @@
 ---
 name: odysseus
-description: Use when the user asks Claude Code to read or write Odysseus data (todos, email, calendar, memory, documents) through the scoped Claude Agent API. Requires ODYSSEUS_URL and ODYSSEUS_API_TOKEN.
+description: Use when the user asks Claude Code to read or write Odysseus data (todos, email, calendar, memory, documents) or to launch/monitor/stop a Cookbook model-serve task through the scoped Claude Agent API. Requires ODYSSEUS_URL and ODYSSEUS_API_TOKEN.
 ---

 # Odysseus
@@ -105,6 +105,49 @@ python3 ~/.claude/skills/odysseus/scripts/odysseus_api.py POST /api/codex/memory
 - `POST /api/codex/emails/draft` — body matches `SendEmailRequest` (`to`, `cc`, `bcc`, `subject`, `body`, `body_html`, `attachments`, `account_id`, `in_reply_to`, `references`). Requires `email:draft` (or `email:send`).
 - `POST /api/codex/emails/send` — same body. Requires `email:send`. Never send without explicit user instruction.

+## Cookbook serve (debug a failing model launch)
+
+The Cookbook surface lets you reproduce what a human would do in Odysseus → Cookbook: read which serves are running, tail their tmux output to see why they crashed, edit the launch command, relaunch, kill a stuck one. Use this when the user is debugging a model server that won't come up (compute-capability errors, OOM, missing kernels, wrong attention backend, etc.).
+
+- `GET /api/codex/cookbook/tasks` — list active serve/download/install tasks (sessionId, type, status, repo_id, remoteHost, payload._cmd). Requires `cookbook:read`.
+- `GET /api/codex/cookbook/servers` — list configured servers (name, host, port, env type + path, model dirs). Requires `cookbook:read`.
+- `GET /api/codex/cookbook/cached?host=<NAME>` — list models already cached on the named server (HF cache + Ollama + extra modelDirs). Call BEFORE `serve` to see what's already on disk. Requires `cookbook:read`.
+- `GET /api/codex/cookbook/presets` — list saved serve presets (model + host + port + cmd). The user's saved preset usually has a working cmd — try `preset NAME` before composing your own. Requires `cookbook:read`.
+- `GET /api/codex/cookbook/output/{session_id}?tail=400` — read the last N lines of the task's persistent log file (preferred) or tmux pane (fallback). The log file persists across vllm crashes, so this returns the actual Python traceback even after the bash prompt + neofetch banner overwrites the pane. Default tail=400. Requires `cookbook:read`.
+- `POST /api/codex/cookbook/serve` — launch a serve task. Body matches `ServeRequest`: `{ repo_id, cmd, remote_host?, ssh_port?, env_prefix?, gpus?, platform? }`. The `cmd` is validated: leading binary must be `vllm`/`python3`/`sglang`/`llama-server`/`ollama`/`node`/`npx`. NEVER prefix with `cd …`, `source …`, or chain with `&&`/`||`/`;`/`$(...)` — the validator rejects shell metacharacters. The venv activation (`env_prefix`) is added automatically from the host's saved settings, so pass the bare binary + args. Requires `cookbook:launch`.
+- `POST /api/codex/cookbook/preset/{name}` — launch a saved preset by name. Reuses the working cmd + host the user already saved. Requires `cookbook:launch`.
+- `POST /api/codex/cookbook/adopt` — register an externally-launched tmux session into cookbook tracking. Body: `{ tmux_session, model, host?, port? }`. Use this when serve_model rejected a cmd and you fell back to direct ssh+tmux — without adoption, the session is invisible to the UI. Requires `cookbook:launch`.
+- `POST /api/codex/cookbook/stop/{session_id}` — kill the tmux session for that task. Requires `cookbook:launch`.
+
+```bash
+# Survey what's running
+python3 ~/.claude/skills/odysseus/scripts/odysseus_api.py cookbook tasks
+
+# Tail the failing one (sessionId from `cookbook tasks`)
+python3 ~/.claude/skills/odysseus/scripts/odysseus_api.py cookbook output serve-abc12345 400
+
+# Stop the previous attempt before you try a new flag set
+python3 ~/.claude/skills/odysseus/scripts/odysseus_api.py cookbook stop serve-abc12345
+
+# Relaunch with new flags. cmd MUST begin with one of the allowlisted binaries.
+python3 ~/.claude/skills/odysseus/scripts/odysseus_api.py cookbook serve \
+  /mnt/HADES/models/Qwen3.5-397B-A17B-AWQ \
+  "vllm serve /mnt/HADES/models/Qwen3.5-397B-A17B-AWQ --host 0.0.0.0 --port 8001 --tensor-parallel-size 8 --max-model-len 262144 --gpu-memory-utilization 0.90 --dtype auto --max-num-seqs 8 --trust-remote-code --enable-expert-parallel --enable-auto-tool-choice --tool-call-parser qwen3_coder --reasoning-parser qwen3" \
+  pewds@192.168.1.12
+```
+
+**Debug loop pattern:** when a serve is failing, the productive sequence is
+
+1. `cookbook tasks` → find the failing sessionId.
+2. `cookbook output SID 600` → read the last 600 lines, find the actual root-cause line (often above the visible tail because tmux scrollback rolled — request a larger `tail` if the error references "above").
+3. `cookbook stop SID` — kill the previous attempt before relaunching; two serves on the same `--port` collide.
+4. `cookbook serve repo "new cmd"` — try the next variation. Wait ~20s, then `cookbook output` on the new sessionId.
+
+**Hard limits this surface enforces:**
+- `cookbook serve` cmd allowlist + shell-metacharacter rejection — you cannot run arbitrary shell, only model-server binaries.
+- `cookbook stop` only targets task sessionIds matching `[a-zA-Z0-9_-]+`.
+- The agent CAN spawn GPU-pinning long-lived processes — always `cookbook stop` your previous attempt before relaunching, and check `cookbook tasks` for collisions on the same `--port` before launching.
+
 ## Forbidden Bypass Pattern

 If you are about to reach the Odysseus host/container, import app internals, query the database, or call MCP helper modules directly, stop. Those paths bypass Odysseus Settings and token scopes. Ask the user to enable the relevant Claude Agent tool toggle instead.
@@ -17,6 +17,15 @@ def _usage() -> int:
    print("  odysseus_api.py todos add TITLE", file=sys.stderr)
    print("  odysseus_api.py emails list [limit]", file=sys.stderr)
    print("  odysseus_api.py emails read UID", file=sys.stderr)
+    print("  odysseus_api.py cookbook tasks", file=sys.stderr)
+    print("  odysseus_api.py cookbook servers", file=sys.stderr)
+    print("  odysseus_api.py cookbook cached [HOST]", file=sys.stderr)
+    print("  odysseus_api.py cookbook presets", file=sys.stderr)
+    print("  odysseus_api.py cookbook output SESSION_ID [tail]", file=sys.stderr)
+    print("  odysseus_api.py cookbook serve REPO_ID 'CMD' [REMOTE_HOST]", file=sys.stderr)
+    print("  odysseus_api.py cookbook preset NAME", file=sys.stderr)
+    print("  odysseus_api.py cookbook adopt SESSION_ID MODEL [HOST] [PORT]", file=sys.stderr)
+    print("  odysseus_api.py cookbook stop SESSION_ID", file=sys.stderr)
    print("  odysseus_api.py METHOD /api/codex/path [json-body]", file=sys.stderr)
    return 2

@@ -72,6 +81,61 @@ def main() -> int:
            body = None
        else:
            return _usage()
+    elif command == "cookbook":
+        if len(sys.argv) < 3:
+            return _usage()
+        action = sys.argv[2].lower()
+        if action == "tasks":
+            method = "GET"
+            path = "/api/codex/cookbook/tasks"
+            body = None
+        elif action == "servers":
+            method = "GET"
+            path = "/api/codex/cookbook/servers"
+            body = None
+        elif action == "output" and len(sys.argv) >= 4:
+            method = "GET"
+            sid = sys.argv[3]
+            tail = sys.argv[4] if len(sys.argv) >= 5 else "400"
+            path = f"/api/codex/cookbook/output/{sid}?tail={tail}"
+            body = None
+        elif action == "cached":
+            method = "GET"
+            if len(sys.argv) >= 4:
+                from urllib.parse import quote
+                path = f"/api/codex/cookbook/cached?host={quote(sys.argv[3])}"
+            else:
+                path = "/api/codex/cookbook/cached"
+            body = None
+        elif action == "presets":
+            method = "GET"
+            path = "/api/codex/cookbook/presets"
+            body = None
+        elif action == "preset" and len(sys.argv) >= 4:
+            from urllib.parse import quote
+            method = "POST"
+            path = f"/api/codex/cookbook/preset/{quote(sys.argv[3])}"
+            body = None
+        elif action == "adopt" and len(sys.argv) >= 5:
+            method = "POST"
+            path = "/api/codex/cookbook/adopt"
+            payload = {"tmux_session": sys.argv[3], "model": sys.argv[4]}
+            if len(sys.argv) >= 6: payload["host"] = sys.argv[5]
+            if len(sys.argv) >= 7: payload["port"] = int(sys.argv[6])
+            body = json.dumps(payload)
+        elif action == "serve" and len(sys.argv) >= 5:
+            method = "POST"
+            path = "/api/codex/cookbook/serve"
+            payload = {"repo_id": sys.argv[3], "cmd": sys.argv[4]}
+            if len(sys.argv) >= 6:
+                payload["remote_host"] = sys.argv[5]
+            body = json.dumps(payload)
+        elif action == "stop" and len(sys.argv) >= 4:
+            method = "POST"
+            path = f"/api/codex/cookbook/stop/{sys.argv[3]}"
+            body = None
+        else:
+            return _usage()
    else:
        if len(sys.argv) < 3:
            return _usage()
@@ -17,6 +17,15 @@ def _usage() -> int:
    print("  odysseus_api.py todos add TITLE", file=sys.stderr)
    print("  odysseus_api.py emails list [limit]", file=sys.stderr)
    print("  odysseus_api.py emails read UID", file=sys.stderr)
+    print("  odysseus_api.py cookbook tasks", file=sys.stderr)
+    print("  odysseus_api.py cookbook servers", file=sys.stderr)
+    print("  odysseus_api.py cookbook cached [HOST]", file=sys.stderr)
+    print("  odysseus_api.py cookbook presets", file=sys.stderr)
+    print("  odysseus_api.py cookbook output SESSION_ID [tail]", file=sys.stderr)
+    print("  odysseus_api.py cookbook serve REPO_ID 'CMD' [REMOTE_HOST]", file=sys.stderr)
+    print("  odysseus_api.py cookbook preset NAME", file=sys.stderr)
+    print("  odysseus_api.py cookbook adopt SESSION_ID MODEL [HOST] [PORT]", file=sys.stderr)
+    print("  odysseus_api.py cookbook stop SESSION_ID", file=sys.stderr)
    print("  odysseus_api.py METHOD /api/codex/path [json-body]", file=sys.stderr)
    return 2

@@ -72,6 +81,61 @@ def main() -> int:
            body = None
        else:
            return _usage()
+    elif command == "cookbook":
+        if len(sys.argv) < 3:
+            return _usage()
+        action = sys.argv[2].lower()
+        if action == "tasks":
+            method = "GET"
+            path = "/api/codex/cookbook/tasks"
+            body = None
+        elif action == "servers":
+            method = "GET"
+            path = "/api/codex/cookbook/servers"
+            body = None
+        elif action == "output" and len(sys.argv) >= 4:
+            method = "GET"
+            sid = sys.argv[3]
+            tail = sys.argv[4] if len(sys.argv) >= 5 else "400"
+            path = f"/api/codex/cookbook/output/{sid}?tail={tail}"
+            body = None
+        elif action == "cached":
+            method = "GET"
+            if len(sys.argv) >= 4:
+                from urllib.parse import quote
+                path = f"/api/codex/cookbook/cached?host={quote(sys.argv[3])}"
+            else:
+                path = "/api/codex/cookbook/cached"
+            body = None
+        elif action == "presets":
+            method = "GET"
+            path = "/api/codex/cookbook/presets"
+            body = None
+        elif action == "preset" and len(sys.argv) >= 4:
+            from urllib.parse import quote
+            method = "POST"
+            path = f"/api/codex/cookbook/preset/{quote(sys.argv[3])}"
+            body = None
+        elif action == "adopt" and len(sys.argv) >= 5:
+            method = "POST"
+            path = "/api/codex/cookbook/adopt"
+            payload = {"tmux_session": sys.argv[3], "model": sys.argv[4]}
+            if len(sys.argv) >= 6: payload["host"] = sys.argv[5]
+            if len(sys.argv) >= 7: payload["port"] = int(sys.argv[6])
+            body = json.dumps(payload)
+        elif action == "serve" and len(sys.argv) >= 5:
+            method = "POST"
+            path = "/api/codex/cookbook/serve"
+            payload = {"repo_id": sys.argv[3], "cmd": sys.argv[4]}
+            if len(sys.argv) >= 6:
+                payload["remote_host"] = sys.argv[5]
+            body = json.dumps(payload)
+        elif action == "stop" and len(sys.argv) >= 4:
+            method = "POST"
+            path = f"/api/codex/cookbook/stop/{sys.argv[3]}"
+            body = None
+        else:
+            return _usage()
    else:
        if len(sys.argv) < 3:
            return _usage()
@@ -1,6 +1,6 @@
 ---
 name: odysseus
-description: Use when the user asks Codex to read or write Odysseus data from a terminal Codex session through the scoped Codex Agent API. Requires ODYSSEUS_URL and ODYSSEUS_API_TOKEN.
+description: Use when the user asks Codex to read or write Odysseus data (todos, email, calendar, memory, documents) or to launch/monitor/stop a Cookbook model-serve task through the scoped Codex Agent API. Requires ODYSSEUS_URL and ODYSSEUS_API_TOKEN.
 ---

 # Odysseus
@@ -105,6 +105,37 @@ python3 integrations/codex/scripts/odysseus_api.py POST /api/codex/memory '{"tex
 - `POST /api/codex/emails/draft` — body matches `SendEmailRequest` (`to`, `cc`, `bcc`, `subject`, `body`, `body_html`, `attachments`, `account_id`, `in_reply_to`, `references`). Requires `email:draft` (or `email:send`).
 - `POST /api/codex/emails/send` — same body. Requires `email:send`. Never send without explicit user instruction.

+## Cookbook serve (debug a failing model launch)
+
+The Cookbook surface lets you reproduce what a human would do in Odysseus → Cookbook: read which serves are running, tail their tmux output to see why they crashed, edit the launch command, relaunch, kill a stuck one. Use this when the user is debugging a model server that won't come up (compute-capability errors, OOM, missing kernels, wrong attention backend, etc.).
+
+- `GET /api/codex/cookbook/tasks` — list active serve/download/install tasks (sessionId, type, status, repo_id, remoteHost, payload._cmd). Requires `cookbook:read`.
+- `GET /api/codex/cookbook/servers` — list configured servers (name, host, port, env type + path, model dirs). Requires `cookbook:read`.
+- `GET /api/codex/cookbook/cached?host=<NAME>` — list models already cached on the named server (HF cache + Ollama + extra modelDirs). Call BEFORE `serve` to see what's already on disk. Requires `cookbook:read`.
+- `GET /api/codex/cookbook/presets` — list saved serve presets (model + host + port + cmd). The user's saved preset usually has a working cmd — try `preset NAME` before composing your own. Requires `cookbook:read`.
+- `GET /api/codex/cookbook/output/{session_id}?tail=400` — read the last N lines of the task's persistent log file (preferred) or tmux pane (fallback). The log file persists across vllm crashes, so this returns the actual Python traceback even after the bash prompt + neofetch banner overwrites the pane. Default tail=400. Requires `cookbook:read`.
+- `POST /api/codex/cookbook/serve` — launch a serve task. Body matches `ServeRequest`: `{ repo_id, cmd, remote_host?, ssh_port?, env_prefix?, gpus?, platform? }`. The `cmd` is validated: leading binary must be `vllm`/`python3`/`sglang`/`llama-server`/`ollama`/`node`/`npx`. NEVER prefix with `cd …`, `source …`, or chain with `&&`/`||`/`;`/`$(...)` — the validator rejects shell metacharacters. The venv activation (`env_prefix`) is added automatically from the host's saved settings, so pass the bare binary + args. Requires `cookbook:launch`.
+- `POST /api/codex/cookbook/preset/{name}` — launch a saved preset by name. Reuses the working cmd + host the user already saved. Requires `cookbook:launch`.
+- `POST /api/codex/cookbook/adopt` — register an externally-launched tmux session into cookbook tracking. Body: `{ tmux_session, model, host?, port? }`. Use this when serve_model rejected a cmd and you fell back to direct ssh+tmux — without adoption, the session is invisible to the UI. Requires `cookbook:launch`.
+- `POST /api/codex/cookbook/stop/{session_id}` — kill the tmux session. Requires `cookbook:launch`.
+
+```bash
+python3 ~/plugins/odysseus/scripts/odysseus_api.py cookbook tasks
+python3 ~/plugins/odysseus/scripts/odysseus_api.py cookbook output serve-abc12345 400
+python3 ~/plugins/odysseus/scripts/odysseus_api.py cookbook stop serve-abc12345
+python3 ~/plugins/odysseus/scripts/odysseus_api.py cookbook serve \
+  /mnt/HADES/models/Qwen3.5-397B-A17B-AWQ \
+  "vllm serve /mnt/HADES/models/Qwen3.5-397B-A17B-AWQ --host 0.0.0.0 --port 8001 --tensor-parallel-size 8 --max-model-len 262144 --gpu-memory-utilization 0.90 --dtype auto --max-num-seqs 8 --trust-remote-code --enable-expert-parallel --enable-auto-tool-choice --tool-call-parser qwen3_coder --reasoning-parser qwen3" \
+  pewds@192.168.1.12
+```
+
+**Debug loop pattern:** `tasks` → `output SID 600` (find root cause; request larger `tail` if it references "above") → `stop SID` → `serve repo "new cmd"` → wait ~20s → `output` on the new sessionId.
+
+**Hard limits this surface enforces:**
+- `cookbook serve` cmd allowlist + shell-metacharacter rejection.
+- `cookbook stop` requires sessionIds matching `[a-zA-Z0-9_-]+`.
+- Agent CAN spawn GPU-pinning long-lived processes — always `cookbook stop` your previous attempt before relaunching.
+
 ## Forbidden Bypass Pattern

 If you are about to reach the Odysseus host/container, import app internals, query the database, or call MCP helper modules directly, stop. Those paths bypass Odysseus Settings and token scopes. Ask the user to enable the relevant Codex Agent tool toggle instead.
@@ -1,22 +0,0 @@
-"""
-_common.py
-
-Shared constants and helpers for built-in MCP servers.
-"""
-
-MAX_OUTPUT_CHARS = 10_000
-MAX_READ_CHARS = 20_000
-SHELL_TIMEOUT = 60
-PYTHON_TIMEOUT = 30
-SEARCH_TIMEOUT = 30
-
-
-def truncate(text: str, limit: int = MAX_OUTPUT_CHARS) -> str:
-    """Truncate text to *limit* characters with a suffix note."""
-    if not isinstance(text, str):
-        # Tool output is occasionally None or a non-string; len(None) would
-        # raise. Coerce so this shared helper never crashes a tool response.
-        text = "" if text is None else str(text)
-    if len(text) > limit:
-        return text[:limit] + f"\n... (truncated, {len(text)} chars total)"
-    return text
@@ -16,6 +16,8 @@ from mcp.types import Tool, TextContent

 sys.path.insert(0, str(Path(__file__).resolve().parent.parent))

+from src.constants import GENERATED_IMAGES_DIR
+
 server = Server("image_gen")


@@ -115,14 +117,18 @@ async def call_tool(name: str, arguments: dict) -> list[TextContent]:

            img = images[0]
            image_url = None
+            # Prefix the instance's public base URL (existing app_public_url setting) so the
+            # link is fully-qualified and clickable when the model echoes it. Empty = relative
+            # same-origin path (unchanged default).
+            _pub_base = (get_setting("app_public_url", "") or "").rstrip("/")

            if img.get("b64_json"):
-                img_dir = Path("data/generated_images")
+                img_dir = Path(GENERATED_IMAGES_DIR)
                img_dir.mkdir(parents=True, exist_ok=True)
                filename = f"{uuid.uuid4().hex[:12]}.png"
                img_path = img_dir / filename
                img_path.write_bytes(base64.b64decode(img["b64_json"]))
-                image_url = f"/api/generated-image/{filename}"
+                image_url = f"{_pub_base}/api/generated-image/{filename}"

                # Save to gallery
                try:
@@ -146,7 +152,13 @@ async def call_tool(name: str, arguments: dict) -> list[TextContent]:
            else:
                return [TextContent(type="text", text="Error: Unexpected image API response format")]

-            result = f"Generated image for: {prompt[:100]}\nimage_url: {image_url}\nmodel: {model_id}\nsize: {size}"
+            # "Direct link:" rather than an "image_url:" label — small models copied the
+            # label token ("image_url") into the link href, producing a broken link.
+            result = (
+                f"Generated image for: {prompt[:100]}\n"
+                f"Direct link: {image_url}\n"
+                f"model: {model_id}\nsize: {size}"
+            )
            return [TextContent(type="text", text=result)]

    except httpx.TimeoutException:
@@ -1,5 +1,5 @@
 {
-  "name": "odysseus-ui",
+  "name": "odysseus",
  "lockfileVersion": 3,
  "requires": true,
  "packages": {
@@ -1,3 +1,18 @@
 [tool.pytest.ini_options]
 testpaths = ["tests"]
 asyncio_mode = "auto"
+# Test-taxonomy markers added at collection time by tests/conftest.py. The
+# stable area_* markers are declared here; the dynamic sub_<filename-token>
+# markers are registered before collection by pytest_configure in
+# tests/conftest.py, so unknown-mark warnings still flag genuine typos outside
+# the taxonomy. See tests/_taxonomy.py and tests/README.md.
+markers = [
+    "area_security: tests covering auth, owner-scope, SSRF, XSS, confinement, redaction",
+    "area_routes: tests covering HTTP route / API behavior",
+    "area_services: tests covering service-layer behavior (llm, cookbook, email, calendar, ...)",
+    "area_cli: tests covering CLI / script behavior",
+    "area_js: JavaScript / Node-backed tests",
+    "area_helpers: self-tests for the shared test helpers in tests/helpers/",
+    "area_unit: pure parser / utility tests that do not clearly belong elsewhere",
+    "area_uncategorized: tests not yet matched by the taxonomy (fallback)",
+]
@@ -31,7 +31,7 @@ from core.database import (
    CalendarEvent,
    CalendarCal,
 )
-from src.constants import DATA_DIR
+from src.constants import DATA_DIR, SKILLS_DIR, SKILLS_FILE, GALLERY_DIR, GALLERY_UPLOADS_DIR

 logger = logging.getLogger(__name__)

@@ -107,7 +107,7 @@ def setup_admin_wipe_routes(session_manager):
                # Skills live as SKILL.md files under data/skills/. Drop
                # the entire directory; the SkillsManager re-creates the
                # tree on next write.
-                skills_dir = os.path.join(DATA_DIR, "skills")
+                skills_dir = SKILLS_DIR
                count = 0
                if os.path.isdir(skills_dir):
                    # Count SKILL.md files for the response — quick walk.
@@ -115,7 +115,7 @@ def setup_admin_wipe_routes(session_manager):
                        count += sum(1 for f in files if f == "SKILL.md")
                    _rmtree_quiet(skills_dir)
                # Legacy fallback file
-                legacy = os.path.join(DATA_DIR, "skills.json")
+                legacy = SKILLS_FILE
                if os.path.exists(legacy):
                    try:
                        os.remove(legacy)
@@ -151,8 +151,8 @@ def setup_admin_wipe_routes(session_manager):
                db.query(GalleryAlbum).delete()
                db.commit()
                # Also drop the upload dir so disk doesn't keep orphans.
-                _rmtree_quiet(os.path.join(DATA_DIR, "gallery"))
-                _rmtree_quiet(os.path.join(DATA_DIR, "gallery_uploads"))
+                _rmtree_quiet(GALLERY_DIR)
+                _rmtree_quiet(GALLERY_UPLOADS_DIR)
                return {"status": "deleted", "kind": kind, "count": count}

            if kind == "calendar":
@@ -25,6 +25,8 @@ ALLOWED_SCOPES = {
    "calendar:write",
    "memory:read",
    "memory:write",
+    "cookbook:read",
+    "cookbook:launch",
 }
 TOKEN_PROFILES = {
    "chat": ["chat"],
@@ -155,22 +157,30 @@ def setup_api_token_routes() -> APIRouter:
            payload = await request.json()
        except Exception:
            payload = {}
-        scope_list = _normalize_scopes(payload.get("scopes"))
-        scopes_value = ",".join(scope_list)
        with get_db_session() as db:
            token = db.query(ApiToken).filter(ApiToken.id == token_id).first()
            if not token:
                raise HTTPException(404, "Token not found")
            if isinstance(payload.get("name"), str) and payload["name"].strip():
                token.name = payload["name"].strip()[:MAX_NAME_LEN]
-            token.scopes = scopes_value
+            # Only touch scopes when the caller actually sent them. A partial
+            # update such as a rename ({"name": ...} with no "scopes" key) must
+            # not silently reset the token to the default scope — that dropped
+            # every previously granted scope.
+            if "scopes" in payload:
+                token.scopes = ",".join(_normalize_scopes(payload.get("scopes")))
            db.add(token)
+            current_scopes = [
+                s.strip()
+                for s in (getattr(token, "scopes", "") or DEFAULT_SCOPES).split(",")
+                if s.strip()
+            ]
            response = {
                "id": token_id,
                "name": getattr(token, "name", ""),
                "owner": getattr(token, "owner", None),
                "token_prefix": getattr(token, "token_prefix", ""),
-                "scopes": scope_list,
+                "scopes": current_scopes,
            }
        _invalidate_cache(request)
        return response
@@ -131,10 +131,8 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
                return {"ok": False, "requires_totp": True, "username": username}
            if not auth_manager.totp_verify(username, body.totp_code):
                raise HTTPException(401, "Invalid 2FA code")
-        # All checks passed — create session
-        token = await asyncio.to_thread(auth_manager.create_session, username, body.password)
-        if not token:
-            raise HTTPException(401, "Invalid credentials")
+        # All checks passed — create session (password already verified above)
+        token = await asyncio.to_thread(auth_manager.create_session_trusted, username)
        cookie_kwargs = dict(
            key=SESSION_COOKIE,
            value=token,
@@ -585,6 +583,27 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
                    hint = " If this is Docker Compose ntfy, set NTFY_BIND to that host/Tailscale IP and NTFY_BASE_URL to the same server URL in .env, then recreate ntfy."
                return {"ok": False, "message": f"ntfy publish to {full_url} failed: {e}.{hint}"[:500]}

+        if preset == "discord_webhook":
+            import httpx
+            webhook_url = (integ.get("base_url") or "").strip()
+            if not webhook_url:
+                return {"ok": False, "message": "No webhook URL set — paste the full Discord webhook URL into the Base URL field."}
+            payload = {
+                "embeds": [{
+                    "title": "Odysseus connectivity test",
+                    "description": "If you see this, your Discord Webhook integration is wired up correctly.",
+                    "color": 5793266,
+                }]
+            }
+            try:
+                async with httpx.AsyncClient(timeout=8.0) as client:
+                    r = await client.post(webhook_url, json=payload)
+                if r.is_success:
+                    return {"ok": True, "message": "Test embed sent — check your Discord channel to confirm it arrived."}
+                return {"ok": False, "message": f"Discord returned HTTP {r.status_code}: {r.text[:200]}"}
+            except Exception as e:
+                return {"ok": False, "message": f"Request failed: {e}"[:400]}
+
        # All other presets: GET against a known health endpoint.
        # Fall back to detecting from name if preset is missing.
        health_paths = {
@@ -101,24 +101,68 @@ def setup_backup_routes(memory_manager, preset_manager, skills_manager) -> APIRo
        # ── Skills ──
        if "skills" in body and isinstance(body["skills"], list):
            existing = skills_manager.load_all()
-            existing_ids = {s.get("id") for s in existing}
-            existing_titles = {s.get("title", "").strip().lower() for s in existing}
+            existing_names = {s.get("name") for s in existing if s.get("name")}
+            existing_ids = {s.get("id") for s in existing if s.get("id")}
+            existing_titles = {
+                (s.get("title") or s.get("description") or "").strip().lower()
+                for s in existing
+            }
            added = 0
            for skill in body["skills"]:
-                if not isinstance(skill, dict) or not skill.get("title"):
+                if not isinstance(skill, dict):
                    continue
-                # Skip if same id or same title already exists
-                if skill.get("id") in existing_ids:
+                title = (
+                    skill.get("title") or skill.get("description")
+                    or skill.get("name") or ""
+                ).strip()
+                if not title:
                    continue
-                if skill["title"].strip().lower() in existing_titles:
+                sid = skill.get("id") or skill.get("name")
+                if sid and sid in existing_ids:
                    continue
-                if user and not skill.get("owner"):
-                    skill["owner"] = user
-                existing.append(skill)
-                existing_ids.add(skill.get("id"))
-                existing_titles.add(skill["title"].strip().lower())
+                nm = skill.get("name")
+                if nm and nm in existing_names:
+                    continue
+                if title.lower() in existing_titles:
+                    continue
+                owner = skill.get("owner")
+                if user and not owner:
+                    owner = user
+                # Skills live on disk as SKILL.md files; the old JSON-era
+                # skills_manager.save() no longer exists. Write each new skill
+                # via add_skill (source="user" skips auto-dedup — this is an
+                # explicit backup restore).
+                result = skills_manager.add_skill(
+                    title=title,
+                    name=skill.get("name"),
+                    description=skill.get("description"),
+                    problem=skill.get("problem", ""),
+                    solution=skill.get("solution", ""),
+                    steps=skill.get("steps"),
+                    tags=skill.get("tags"),
+                    source="user",
+                    teacher_model=skill.get("teacher_model"),
+                    confidence=skill.get("confidence", 0.8),
+                    owner=owner,
+                    category=skill.get("category", "general"),
+                    when_to_use=skill.get("when_to_use"),
+                    procedure=skill.get("procedure"),
+                    pitfalls=skill.get("pitfalls"),
+                    verification=skill.get("verification"),
+                    platforms=skill.get("platforms"),
+                    requires_toolsets=skill.get("requires_toolsets"),
+                    fallback_for_toolsets=skill.get("fallback_for_toolsets"),
+                    status=skill.get("status", "draft"),
+                    version=skill.get("version", "1.0.0"),
+                )
+                if result.get("_deduped"):
+                    continue
+                if result.get("name"):
+                    existing_names.add(result["name"])
+                if result.get("id"):
+                    existing_ids.add(result["id"])
+                existing_titles.add(title.lower())
                added += 1
-            skills_manager.save(existing)
            imported.append(f"{added} skills")

        # ── Presets ──
@@ -1,6 +1,7 @@
 """Calendar routes — local SQLite-backed calendar CRUD."""

 import logging
+import re
 import uuid
 from datetime import datetime, date, timedelta
 from typing import Optional, List
@@ -12,7 +13,7 @@ from dateutil.rrule import rrulestr

 from core.database import SessionLocal, CalendarCal, CalendarEvent
 from src.auth_helpers import require_user
-from src.upload_limits import read_upload_limited
+from src.upload_limits import read_upload_limited, ICS_MAX_BYTES

 logger = logging.getLogger(__name__)

@@ -100,6 +101,15 @@ def _ics_escape(text: str) -> str:
    )


+def _safe_ics_filename(name: str) -> str:
+    """Return a conservative .ics filename safe for Content-Disposition."""
+    stem = name if isinstance(name, str) else ""
+    stem = re.sub(r"[^A-Za-z0-9._-]", "_", stem).strip("._-")
+    if not stem:
+        stem = "calendar"
+    return f"{stem[:128]}.ics"
+
+
 def _resolve_base_uid(uid: str) -> str:
    """Extract the base series UID from a compound occurrence UID.

@@ -248,6 +258,17 @@ def parse_due_for_user(s: str) -> str:
        if t is not None:
            return base.replace(hour=t[0], minute=t[1]).isoformat()

+    # Time-first: "3pm today", "11pm today", "9am tomorrow"
+    m = _re.match(r'^(.+?)\s+(today|tonight|tomorrow|tmrw|yesterday)$', lower)
+    if m:
+        time_part, word = m.group(1).strip(), m.group(2)
+        base = today
+        if word in ("tomorrow", "tmrw"): base = today + _td(days=1)
+        elif word == "yesterday":        base = today - _td(days=1)
+        t = _parse_time(time_part)
+        if t is not None:
+            return base.replace(hour=t[0], minute=t[1]).isoformat()
+
    m = _re.match(r'^in\s+(\d+)\s*(hour|hr|minute|min|day)s?\s*$', lower)
    if m:
        n = int(m.group(1)); unit = m.group(2)
@@ -399,7 +420,17 @@ def _parse_dt(s: str) -> datetime:
    # Last resort: dateutil's fuzzy parser
    try:
        from dateutil import parser as _du
-        return _du.parse(s)
+        parsed = _du.parse(s)
+        # Strip tz like every other return path above — this function's
+        # contract is naive datetimes (CalendarEvent.dtstart is naive). An
+        # offset-bearing non-ISO input (e.g. RFC-2822 "Mon, 05 Jan 2026
+        # 14:00:00 +0900") otherwise leaked tz-aware into the naive column and
+        # crashed read-back comparisons in _expand_rrule with "can't compare
+        # offset-naive and offset-aware datetimes".
+        if parsed.tzinfo is not None:
+            from datetime import timezone as _tz
+            return parsed.astimezone(_tz.utc).replace(tzinfo=None)
+        return parsed
    except Exception:
        raise ValueError(f"could not parse datetime: {s!r}")

@@ -440,6 +471,9 @@ def _event_to_dict(ev: CalendarEvent) -> dict:

 # ── Recurrence expansion ──

+_RRULE_EXPANSION_LIMIT = 1000
+
+
 def _expand_rrule(
    ev: CalendarEvent, start: datetime, end: datetime
 ) -> List[dict]:
@@ -462,6 +496,7 @@ def _expand_rrule(
        d = _event_to_dict(ev)
        d["is_recurrence"] = False
        d["series_uid"] = ev.uid
+        d["truncated"] = False
        return [d]

    # Parse the rrule, applying it to the base dtstart.
@@ -487,6 +522,7 @@ def _expand_rrule(
        d = _event_to_dict(ev)
        d["is_recurrence"] = False
        d["series_uid"] = ev.uid
+        d["truncated"] = False
        # Malformed RRULE rows are fetched by the recurring SQL branch
        # with only dtstart < end_dt — the base event may not actually
        # overlap the window. Only return if it does.
@@ -499,22 +535,26 @@ def _expand_rrule(
    # (matching non-recurring overlap semantics: dtstart < end AND
    # dtend > start).
    expand_start = start - duration
-    occurrences = rule.between(expand_start, end, inc=True)
-    if not occurrences:
-        return []
-
    results = []
+    truncated = False
    base = _event_to_dict(ev)

-    for occ_start in occurrences:
+    for occ_start in rule.xafter(expand_start, inc=True):
+        if occ_start >= end:
+            break
+
        occ_end = occ_start + duration

        # Overlap filter: occurrence must intersect [start, end).
        # This enforces exclusive-end semantics (occ_start >= end is
        # excluded) and includes multi-day crossings (occ_end > start).
-        if occ_start >= end or occ_end <= start:
+        if occ_end <= start:
            continue

+        if len(results) >= _RRULE_EXPANSION_LIMIT:
+            truncated = True
+            break
+
        # Build the compound uid: {base_uid}::{date} or ::{datetime}
        if ev.all_day:
            occ_uid = f"{ev.uid}::{occ_start.strftime('%Y-%m-%d')}"
@@ -525,6 +565,7 @@ def _expand_rrule(
        d["uid"] = occ_uid
        d["series_uid"] = ev.uid
        d["is_recurrence"] = True
+        d["truncated"] = False

        if ev.all_day:
            d["dtstart"] = occ_start.strftime("%Y-%m-%d")
@@ -537,6 +578,10 @@ def _expand_rrule(

        results.append(d)

+    if truncated:
+        for d in results:
+            d["truncated"] = True
+
    return results


@@ -545,72 +590,178 @@ def _expand_rrule(
 def setup_calendar_routes() -> APIRouter:
    router = APIRouter(prefix="/api/calendar", tags=["calendar"])

-    # CalDAV connect form (Integrations → Calendar). Storage is local
-    # SQLite; sync (src/caldav_sync.py) pulls remote events into it on
-    # calendar open and periodically via the scheduler.
+    # ── CalDAV multi-account helpers ─────────────────────────────────────────
+
+    def _get_caldav_accounts(owner: str) -> list:
+        from src.caldav_sync import _load_caldav_accounts
+        return _load_caldav_accounts(owner)
+
+    def _save_caldav_accounts(owner: str, accounts: list) -> None:
+        from routes.prefs_routes import _load_for_user, _save_for_user
+        prefs = _load_for_user(owner) or {}
+        prefs["caldav_accounts"] = accounts
+        prefs.pop("caldav", None)
+        _save_for_user(owner, prefs)
+
+    # ── CalDAV config routes (backward-compat single-account API) ────────────
+
    @router.get("/config")
    async def get_config(request: Request):
+        """Legacy single-account endpoint — returns the first configured account."""
        owner = _require_user(request)
-        from routes.prefs_routes import _load_for_user
-        cfg = (_load_for_user(owner) or {}).get("caldav", {}) or {}
-        caldav_password = cfg.get("password") or ""
-        if caldav_password:
+        accounts = _get_caldav_accounts(owner)
+        if not accounts:
+            return {"url": "", "username": "", "password": "", "has_password": False, "local": True}
+        first = accounts[0]
+        pw = first.get("password") or ""
+        has_pw = False
+        if pw:
            try:
                from src.secret_storage import decrypt
-                caldav_password = decrypt(caldav_password)
+                has_pw = bool(decrypt(pw))
            except Exception:
-                pass
-        # Surface url+username but never hand the password back to the
-        # client — saved-state UI shouldn't leak the credential.
+                has_pw = bool(pw)
        return {
-            "url": cfg.get("url", "") or "",
-            "username": cfg.get("username", "") or "",
+            "url": first.get("url", "") or "",
+            "username": first.get("username", "") or "",
            "password": "",
-            "has_password": bool(caldav_password),
-            "local": not bool(cfg.get("url")),
+            "has_password": has_pw,
+            "local": not bool(first.get("url")),
        }

    @router.post("/config")
    async def save_config(request: Request):
+        """Legacy single-account endpoint — upserts the first account."""
        owner = _require_user(request)
-        from routes.prefs_routes import _load_for_user, _save_for_user
        try:
            body = await request.json()
        except Exception:
            body = {}
-        prefs = _load_for_user(owner) or {}
-        cfg = dict(prefs.get("caldav") or {})
-        # Empty url => clear the whole entry (treat as "remove integration").
+        accounts = _get_caldav_accounts(owner)
        if not (body.get("url") or "").strip():
-            prefs.pop("caldav", None)
-            _save_for_user(owner, prefs)
+            _save_caldav_accounts(owner, [])
            return {"ok": True, "cleared": True}
        from src.caldav_sync import validate_caldav_url
        try:
-            cfg["url"] = validate_caldav_url(body.get("url", ""))
+            validated_url = validate_caldav_url(body.get("url", ""))
        except ValueError as e:
            raise HTTPException(400, str(e))
-        cfg["username"] = (body.get("username") or "").strip()
-        # Preserve the stored password when the client sends an empty
-        # one (edit form re-submitted without re-typing the password).
-        # cfg already holds the existing (already-encrypted) password from
-        # prefs, so we only touch it when a new password is supplied —
-        # re-encrypting the stored value would double-encrypt it.
+        if accounts:
+            acc = dict(accounts[0])
+        else:
+            import uuid as _uuid
+            acc = {"id": str(_uuid.uuid4()), "label": "CalDAV"}
+        acc["url"] = validated_url
+        acc["username"] = (body.get("username") or "").strip()
        if body.get("password"):
            from src.secret_storage import encrypt
-            cfg["password"] = encrypt(body["password"])
-        prefs["caldav"] = cfg
-        _save_for_user(owner, prefs)
+            acc["password"] = encrypt(body["password"])
+        new_accounts = [acc] + (accounts[1:] if len(accounts) > 1 else [])
+        _save_caldav_accounts(owner, new_accounts)
+        return {"ok": True}
+
+    # ── CalDAV multi-account CRUD ─────────────────────────────────────────────
+
+    @router.get("/config/accounts")
+    async def list_caldav_accounts(request: Request):
+        """Return all configured CalDAV accounts (passwords never returned)."""
+        owner = _require_user(request)
+        accounts = _get_caldav_accounts(owner)
+        safe = []
+        for acc in accounts:
+            pw = acc.get("password") or ""
+            has_pw = False
+            if pw:
+                try:
+                    from src.secret_storage import decrypt
+                    has_pw = bool(decrypt(pw))
+                except Exception:
+                    has_pw = bool(pw)
+            safe.append({
+                "id": acc.get("id", ""),
+                "label": acc.get("label", "") or acc.get("url", ""),
+                "url": acc.get("url", "") or "",
+                "username": acc.get("username", "") or "",
+                "has_password": has_pw,
+            })
+        return {"accounts": safe}
+
+    @router.post("/config/accounts")
+    async def add_caldav_account(request: Request):
+        """Add a new CalDAV account."""
+        import uuid as _uuid
+        owner = _require_user(request)
+        try:
+            body = await request.json()
+        except Exception:
+            body = {}
+        from src.caldav_sync import validate_caldav_url
+        try:
+            url = validate_caldav_url(body.get("url", ""))
+        except ValueError as e:
+            raise HTTPException(400, str(e))
+        if not body.get("password"):
+            raise HTTPException(400, "Password is required")
+        from src.secret_storage import encrypt
+        new_acc = {
+            "id": str(_uuid.uuid4()),
+            "label": (body.get("label") or "").strip() or "CalDAV",
+            "url": url,
+            "username": (body.get("username") or "").strip(),
+            "password": encrypt(body["password"]),
+        }
+        accounts = _get_caldav_accounts(owner)
+        accounts.append(new_acc)
+        _save_caldav_accounts(owner, accounts)
+        return {"ok": True, "id": new_acc["id"]}
+
+    @router.put("/config/accounts/{account_id}")
+    async def update_caldav_account(account_id: str, request: Request):
+        """Update an existing CalDAV account by id."""
+        owner = _require_user(request)
+        try:
+            body = await request.json()
+        except Exception:
+            body = {}
+        accounts = _get_caldav_accounts(owner)
+        idx = next((i for i, a in enumerate(accounts) if a.get("id") == account_id), None)
+        if idx is None:
+            raise HTTPException(404, "Account not found")
+        acc = dict(accounts[idx])
+        if body.get("url"):
+            from src.caldav_sync import validate_caldav_url
+            try:
+                acc["url"] = validate_caldav_url(body["url"])
+            except ValueError as e:
+                raise HTTPException(400, str(e))
+        if body.get("label") is not None:
+            acc["label"] = (body.get("label") or "").strip() or "CalDAV"
+        if body.get("username") is not None:
+            acc["username"] = (body.get("username") or "").strip()
+        if body.get("password"):
+            from src.secret_storage import encrypt
+            acc["password"] = encrypt(body["password"])
+        accounts[idx] = acc
+        _save_caldav_accounts(owner, accounts)
+        return {"ok": True}
+
+    @router.delete("/config/accounts/{account_id}")
+    async def delete_caldav_account(account_id: str, request: Request):
+        """Remove a CalDAV account by id."""
+        owner = _require_user(request)
+        accounts = _get_caldav_accounts(owner)
+        new_accounts = [a for a in accounts if a.get("id") != account_id]
+        if len(new_accounts) == len(accounts):
+            raise HTTPException(404, "Account not found")
+        _save_caldav_accounts(owner, new_accounts)
        return {"ok": True}

    @router.post("/test")
    async def test_connection(request: Request):
-        """Actually probe the configured CalDAV server with a PROPFIND
-        request (the same handshake every CalDAV client uses). Accepts
-        an optional {url, username, password} body so the user can test
-        a configuration BEFORE saving it; falls back to the stored
-        creds otherwise. Returns {ok, error?} with a useful message on
-        failure (status code, auth issue, network error)."""
+        """Probe a CalDAV server with a PROPFIND. Accepts an optional body:
+        {url, username, password} to test before saving, or {account_id} to
+        test an already-saved account. Falls back to the first saved account
+        when nothing is provided."""
        owner = _require_user(request)
        try:
            body = await request.json()
@@ -620,19 +771,24 @@ def setup_calendar_routes() -> APIRouter:
        user = (body.get("username") or "").strip()
        pw = body.get("password") or ""
        if not (url and user and pw):
-            # Fall back to saved settings for this user.
-            from routes.prefs_routes import _load_for_user
-            cfg = (_load_for_user(owner) or {}).get("caldav", {}) or {}
-            url = url or (cfg.get("url") or "")
-            user = user or (cfg.get("username") or "")
-            if not pw:
-                pw = cfg.get("password") or ""
-                if pw:
-                    try:
-                        from src.secret_storage import decrypt
-                        pw = decrypt(pw)
-                    except Exception:
-                        pass
+            # Look up a saved account: by id if supplied, else first account.
+            accounts = _get_caldav_accounts(owner)
+            acc = None
+            if body.get("account_id"):
+                acc = next((a for a in accounts if a.get("id") == body["account_id"]), None)
+            if acc is None and accounts:
+                acc = accounts[0]
+            if acc:
+                url = url or (acc.get("url") or "")
+                user = user or (acc.get("username") or "")
+                if not pw:
+                    pw = acc.get("password") or ""
+                    if pw:
+                        try:
+                            from src.secret_storage import decrypt
+                            pw = decrypt(pw)
+                        except Exception:
+                            pass
        if not (url and user and pw):
            return {"ok": False, "error": "Missing URL, username, or password"}
        from src.caldav_sync import validate_caldav_url
@@ -695,6 +851,28 @@ def setup_calendar_routes() -> APIRouter:
        from src.caldav_sync import sync_caldav
        return await sync_caldav(owner)

+    @router.delete("/calendars/{cal_id}")
+    async def delete_calendar(cal_id: str, request: Request):
+        owner = _require_user(request)
+        db = SessionLocal()
+        try:
+            cal = db.query(CalendarCal).filter(
+                CalendarCal.id == cal_id,
+                CalendarCal.owner == owner,
+            ).first()
+            if not cal:
+                raise HTTPException(404, "Calendar not found")
+            db.delete(cal)
+            db.commit()
+            return {"ok": True}
+        except HTTPException:
+            raise
+        except Exception as e:
+            logger.error("Failed to delete calendar %s: %s", cal_id, e)
+            raise HTTPException(500, "Failed to delete calendar")
+        finally:
+            db.close()
+
    @router.get("/calendars")
    async def list_calendars(request: Request):
        owner = _require_user(request)
@@ -703,7 +881,7 @@ def setup_calendar_routes() -> APIRouter:
            _ensure_default_calendar(db, owner)
            cals = db.query(CalendarCal).filter(CalendarCal.owner == owner).all()
            return {"calendars": [
-                {"name": c.name, "href": c.id, "color": c.color}
+                {"name": c.name, "href": c.id, "color": c.color, "source": c.source}
                for c in cals
            ]}
        except HTTPException:
@@ -766,8 +944,12 @@ def setup_calendar_routes() -> APIRouter:
                expanded.extend(_expand_rrule(e, start_dt, end_dt))

            # Sort by occurrence start time for consistent frontend ordering.
+            truncated = any(e.get("truncated") for e in expanded)
            expanded.sort(key=lambda d: d["dtstart"])
-            return {"events": expanded}
+            response: dict = {"events": expanded}
+            if truncated:
+                response["truncated"] = True
+            return response
        except HTTPException:
            raise
        except Exception as e:
@@ -988,9 +1170,9 @@ def setup_calendar_routes() -> APIRouter:
        finally:
            db.close()

-    # 10 MB hard cap on ICS upload. Loading the whole file into memory is
-    # unavoidable with python-icalendar, so an unbounded upload would OOM.
-    _ICS_MAX_BYTES = 10 * 1024 * 1024
+    # Hard cap on ICS upload (ICS_MAX_BYTES, default 10 MB). Loading the whole
+    # file into memory is unavoidable with python-icalendar, so an unbounded
+    # upload would OOM.

    @router.post("/import")
    async def import_ics(request: Request, file: UploadFile = File(...), calendar_name: str = ""):
@@ -1000,7 +1182,7 @@ def setup_calendar_routes() -> APIRouter:
        owner = _require_user(request)
        db = SessionLocal()
        try:
-            content = await read_upload_limited(file, _ICS_MAX_BYTES, "ICS file")
+            content = await read_upload_limited(file, ICS_MAX_BYTES, "ICS file")
            try:
                cal_data = iCal.from_ical(content)
            except Exception as e:
@@ -1168,11 +1350,14 @@ def setup_calendar_routes() -> APIRouter:
            lines.append("END:VCALENDAR")

            ics_data = "\r\n".join(lines)
-            safe_name = cal.name.replace(" ", "_").replace("/", "_")
+            download_name = _safe_ics_filename(cal.name)
            return Response(
                content=ics_data,
                media_type="text/calendar",
-                headers={"Content-Disposition": f'attachment; filename="{safe_name}.ics"'},
+                headers={
+                    "Content-Disposition": f'attachment; filename="{download_name}"',
+                    "X-Content-Type-Options": "nosniff",
+                },
            )
        except HTTPException:
            raise
@@ -1194,7 +1379,7 @@ def setup_calendar_routes() -> APIRouter:
        "tomorrow", "next Tuesday", "in 30 minutes" resolve correctly.
        Uses the "utility" endpoint (small / fast model) to keep latency low.
        """
-        _require_user(request)
+        owner = _require_user(request)
        from src.endpoint_resolver import resolve_endpoint
        from src.llm_core import llm_call_async
        from src.text_helpers import strip_think
@@ -1220,9 +1405,9 @@ def setup_calendar_routes() -> APIRouter:
        if tz_hint:
            set_user_tz_name(tz_hint)

-        url, model, headers = resolve_endpoint("utility")
+        url, model, headers = resolve_endpoint("utility", owner=owner or None)
        if not url:
-            url, model, headers = resolve_endpoint("default")
+            url, model, headers = resolve_endpoint("default", owner=owner or None)
        if not url or not model:
            return {"ok": False, "error": "No LLM endpoint configured"}

@@ -75,7 +75,7 @@ def _enforce_chat_privileges(request, sess) -> None:
    allowlist, or HTTPException(429) if the user has hit their daily message
    cap. No-op for unauthenticated callers or when auth_manager is absent
    (single-user mode). Admins receive ADMIN_PRIVILEGES from get_privileges,
-    which means empty allowed_models / zero cap → no-op for them.
+    which means unrestricted allowed_models / zero cap -> no-op for them.
    """
    try:
        user = get_current_user(request)
@@ -88,8 +88,18 @@ def _enforce_chat_privileges(request, sess) -> None:
        return

    privs = auth_manager.get_privileges(user) or {}
-    allowed = privs.get("allowed_models") or []
-    if allowed and sess.model and sess.model not in allowed:
+
+    # Explicit "block everything" sentinel takes precedence over the
+    # allowlist — it's the only way to distinguish "user clicked [None]"
+    # (block all) from "user clicked [All]" (no restriction), since both
+    # otherwise produce an empty `allowed_models` list.
+    if privs.get("block_all_models"):
+        raise HTTPException(403, f"Your account is not allowed to use model '{sess.model}'.")
+
+    allowed_raw = privs.get("allowed_models")
+    allowed = allowed_raw if isinstance(allowed_raw, list) else []
+    restricted = bool(privs.get("allowed_models_restricted")) or bool(allowed)
+    if restricted and sess.model and sess.model not in allowed:
        raise HTTPException(403, f"Your account is not allowed to use model '{sess.model}'.")

    cap = int(privs.get("max_messages_per_day") or 0)
@@ -194,14 +204,26 @@ def try_fallback_endpoint(sess, session_id: str) -> dict | None:
    Returns {"model": ..., "endpoint_url": ..., "endpoint_name": ...} or None.
    """
    import requests as _req
-    from src.endpoint_resolver import build_chat_url, build_headers, build_models_url, normalize_base
+    from src.endpoint_resolver import (
+        build_chat_url,
+        build_headers,
+        build_models_url,
+        normalize_base,
+        resolve_endpoint_runtime,
+    )
+    from src.chatgpt_subscription import is_chatgpt_subscription_base

    current_url = sess.endpoint_url or ""
+    owner = getattr(sess, "owner", None)
    db = SessionLocal()
    try:
-        endpoints = db.query(ModelEndpoint).filter(
+        q = db.query(ModelEndpoint).filter(
            ModelEndpoint.is_enabled == True
-        ).all()
+        )
+        if owner:
+            from src.auth_helpers import owner_filter
+            q = owner_filter(q, ModelEndpoint, owner)
+        endpoints = q.all()
    finally:
        db.close()

@@ -210,26 +232,33 @@ def try_fallback_endpoint(sess, session_id: str) -> dict | None:
        # Skip current endpoint
        if current_url and base in current_url:
            continue
-        # Quick ping
-        ping_url = build_models_url(base)
-        headers = build_headers(ep.api_key, base)
        try:
-            r = _req.get(ping_url, headers=headers, timeout=5)
-            r.raise_for_status()
-            data = r.json()
-            models = [m.get("id") for m in (data.get("data") or []) if m.get("id")]
-            if not models:
-                models = [
-                    m.get("name") or m.get("model")
-                    for m in (data.get("models") or [])
-                    if m.get("name") or m.get("model")
-                ]
+            base, api_key = resolve_endpoint_runtime(ep, owner=owner)
+        except Exception:
+            continue
+        ping_url = build_models_url(base)
+        headers = build_headers(api_key, base)
+        try:
+            if ping_url:
+                r = _req.get(ping_url, headers=headers, timeout=5)
+                r.raise_for_status()
+                data = r.json()
+                models = [m.get("id") for m in (data.get("data") or []) if m.get("id")]
+                if not models:
+                    models = [
+                        m.get("name") or m.get("model")
+                        for m in (data.get("models") or [])
+                        if m.get("name") or m.get("model")
+                    ]
+            else:
+                models = json.loads(ep.cached_models or "[]")
            if not models:
                continue
            # Found a working endpoint — update session
            new_model = models[0]
            chat_url = build_chat_url(base)
-            new_headers = build_headers(ep.api_key, base)
+            new_headers = build_headers(api_key, base)
+            persisted_headers = {} if is_chatgpt_subscription_base(base) else new_headers

            sess.model = new_model
            sess.endpoint_url = chat_url
@@ -241,7 +270,7 @@ def try_fallback_endpoint(sess, session_id: str) -> dict | None:
                _db.query(DBSession).filter(DBSession.id == session_id).update({
                    "model": new_model,
                    "endpoint_url": chat_url,
-                    "headers": json.dumps(new_headers),
+                    "headers": persisted_headers,
                })
                _db.commit()
            finally:
@@ -275,11 +304,16 @@ def extract_preset(chat_handler, preset_id) -> PresetInfo:
 async def preprocess(
    chat_handler, message, att_ids, sess,
    auto_opened_docs: Optional[list] = None,
+    allow_tool_preprocessing: bool = True,
 ) -> PreprocessedMessage:
    """Run chat_handler.preprocess_message and wrap the result."""
    enhanced, user_content, text_ctx, yt_transcripts, att_meta = (
        await chat_handler.preprocess_message(
-            message, att_ids, sess, auto_opened_docs=auto_opened_docs
+            message,
+            att_ids,
+            sess,
+            auto_opened_docs=auto_opened_docs,
+            allow_tool_preprocessing=allow_tool_preprocessing,
        )
    )
    return PreprocessedMessage(
@@ -329,16 +363,26 @@ def _session_url_matches_endpoint(session_url: str, endpoint_base: str) -> bool:
        return False


+def _has_auth_keys(headers) -> bool:
+    """True if a headers dict carries an Authorization/x-api-key entry."""
+    return isinstance(headers, dict) and any(
+        k.lower() in ('authorization', 'x-api-key') for k in headers
+    )
+
+
 def resolve_session_auth(sess, session_id: str, owner: Optional[str] = None):
    """Ensure session has auth headers — resolve from endpoint DB if missing."""
-    has_auth = sess.headers and isinstance(sess.headers, dict) and any(
-        k.lower() in ('authorization', 'x-api-key') for k in sess.headers
-    )
-    if has_auth:
+    try:
+        from src.chatgpt_subscription import is_chatgpt_subscription_base
+        is_chatgpt_subscription = is_chatgpt_subscription_base(getattr(sess, "endpoint_url", "") or "")
+    except Exception:
+        is_chatgpt_subscription = False
+    has_auth = _has_auth_keys(sess.headers)
+    if has_auth and not is_chatgpt_subscription:
        return

    try:
-        from src.endpoint_resolver import build_headers, normalize_base
+        from src.endpoint_resolver import build_headers, resolve_endpoint_runtime
        db = SessionLocal()
        try:
            target_url = getattr(sess, "endpoint_url", "") or ""
@@ -354,10 +398,30 @@ def resolve_session_auth(sess, session_id: str, owner: Optional[str] = None):
            for ep in q.all():
                if not _session_url_matches_endpoint(target_url, ep.base_url or ""):
                    continue
-                if not ep.api_key:
+                try:
+                    base, api_key = resolve_endpoint_runtime(ep, owner=owner)
+                except Exception as e:
+                    logger.warning("Failed to resolve provider auth for session %s: %s", session_id, e)
+                    return
+                if not api_key:
+                    # No usable key (e.g. ChatGPT Subscription needs re-auth).
+                    return
+                sess.headers = build_headers(api_key, base)
+                if is_chatgpt_subscription:
+                    # The bearer is short-lived and re-resolved per request, so it
+                    # stays request-local and is never written to the plaintext
+                    # sessions.headers column. Proactively strip any bearer an
+                    # older code path may have persisted so it does not linger.
+                    stale_q = db.query(DBSession).filter(DBSession.id == session_id)
+                    if owner:
+                        stale_q = stale_q.filter(DBSession.owner == owner)
+                    stored = stale_q.first()
+                    if stored is not None and _has_auth_keys(stored.headers):
+                        stale_q.update({"headers": {}})
+                        db.commit()
+                        logger.info(f"Cleared persisted ChatGPT Subscription bearer from session {session_id}")
+                    logger.debug(f"Resolved request-local ChatGPT Subscription auth for session {session_id}")
                    return
-                base = normalize_base(ep.base_url or "")
-                sess.headers = build_headers(ep.api_key, base)
                update_q = db.query(DBSession).filter(DBSession.id == session_id)
                if owner:
                    update_q = update_q.filter(DBSession.owner == owner)
@@ -401,7 +465,12 @@ def _normalize_model_id_from_cache(sess) -> Optional[str]:

    db = SessionLocal()
    try:
-        endpoints = db.query(ModelEndpoint).filter(ModelEndpoint.is_enabled == True).all()
+        q = db.query(ModelEndpoint).filter(ModelEndpoint.is_enabled == True)
+        owner = getattr(sess, "owner", None)
+        if owner:
+            from src.auth_helpers import owner_filter
+            q = owner_filter(q, ModelEndpoint, owner)
+        endpoints = q.all()
        for ep in endpoints:
            try:
                if normalize_base(getattr(ep, "base_url", "") or "") != session_base:
@@ -448,6 +517,7 @@ async def build_chat_context(
    webhook_manager=None,
    use_enhanced_message: bool = False,
    agent_mode: bool = False,
+    allow_tool_preprocessing: bool = True,
 ) -> ChatContext:
    """Build the full context (preface + messages) for an LLM call.

@@ -465,6 +535,7 @@ async def build_chat_context(
    preprocessed = await preprocess(
        chat_handler, message, att_ids or [], sess,
        auto_opened_docs=auto_opened_docs,
+        allow_tool_preprocessing=allow_tool_preprocessing,
    )

    # Add user message to history
@@ -483,6 +554,9 @@ async def build_chat_context(
    # Skills injection respects its own enable toggle (mirrors memory_enabled).
    # When off, the "Available skills" index is not added to the prompt.
    skills_enabled = not incognito and uprefs.get("skills_enabled", True)
+    if not allow_tool_preprocessing:
+        mem_enabled = False
+        skills_enabled = False
    logger.debug(
        "Memory enabled=%s for user=%s (incognito=%s, no_memory=%s, pref=%s)",
        mem_enabled, user, incognito, no_memory, uprefs.get("memory_enabled", "NOT_SET"),
@@ -490,11 +564,11 @@ async def build_chat_context(

    # Use RAG?
    use_rag_val = (str(use_rag).lower() != "false") if use_rag is not None else True
-    if incognito:
+    if incognito or not allow_tool_preprocessing:
        use_rag_val = False

    # If pre-fetched search context was provided (compare mode), skip live web search
-    skip_web = bool(search_context)
+    skip_web = bool(search_context) or not allow_tool_preprocessing

    # Build context preface
    # The stream path uses enhanced_message (with CoT/preprocessing applied),
@@ -521,7 +595,7 @@ async def build_chat_context(
    used_memories = getattr(chat_processor, '_last_used_memories', [])

    # Inject pre-fetched search context (compare mode)
-    if search_context:
+    if search_context and allow_tool_preprocessing:
        preface.append(untrusted_context_message("prefetched search context", search_context))

    # YouTube transcripts
@@ -530,7 +604,11 @@ async def build_chat_context(

    # Normalize model ID. Prefer cached endpoint models so group chat does not
    # re-hit slow local /models endpoints on every participant turn.
-    norm = _normalize_model_id_from_cache(sess) or normalize_model_id(sess.endpoint_url, sess.model)
+    norm = _normalize_model_id_from_cache(sess) or normalize_model_id(
+        sess.endpoint_url,
+        sess.model,
+        owner=getattr(sess, "owner", None),
+    )
    if norm:
        sess.model = norm

@@ -539,7 +617,7 @@ async def build_chat_context(

    # Auto-compact
    messages, context_length, was_compacted = await maybe_compact(
-        sess, sess.endpoint_url, sess.model, messages, sess.headers,
+        sess, sess.endpoint_url, sess.model, messages, sess.headers, owner=user,
    )
    messages = trim_for_context(messages, context_length)

@@ -772,7 +850,19 @@ def save_assistant_response(
 ):
    """Add assistant response to session history. In incognito mode, keeps in-memory context but skips DB persistence."""
    md = dict(last_metrics) if last_metrics else {}
-    md["model"] = sess.model
+    def _model_value(value) -> str:
+        if value is None:
+            return ""
+        if not isinstance(value, str):
+            value = str(value)
+        return value.strip()
+
+    requested_model = _model_value(md.get("requested_model") or md.get("selected_model") or getattr(sess, "model", ""))
+    actual_model = _model_value(md.get("model") or md.get("actual_model") or requested_model)
+    if requested_model:
+        md["requested_model"] = requested_model
+    if actual_model:
+        md["model"] = actual_model
    if character_name:
        md["character_name"] = character_name
    if web_sources:
@@ -841,12 +931,13 @@ def run_post_response_tasks(
    skills_manager=None,
    owner: str = None,
    extract_skills: bool = True,
+    allow_background_extraction: bool = True,
 ):
    """Fire background tasks after a completed response: memory extraction, webhooks, auto-name, skill extraction."""
    # Memory extraction — only every 4th message pair to avoid excess LLM calls
    _msg_count = len(sess.history) if hasattr(sess, 'history') else 0
    _should_extract = (_msg_count >= 4) and (_msg_count % 4 == 0)
-    if not incognito and not compare_mode and _should_extract and uprefs.get("auto_memory", True):
+    if allow_background_extraction and not incognito and not compare_mode and _should_extract and uprefs.get("auto_memory", True):
        from services.memory.memory_extractor import extract_and_store
        from src.task_endpoint import resolve_task_endpoint
        t_url, t_model, t_headers = resolve_task_endpoint(
@@ -873,6 +964,7 @@ def run_post_response_tasks(
    )
    if (
        extract_skills
+        and allow_background_extraction
        and auto_skills_enabled
        and not incognito
        and not compare_mode
@@ -20,6 +20,7 @@ from src import agent_runs
 from src.model_context import estimate_tokens
 from src.chat_helpers import coerce_message_and_session
 from src.endpoint_resolver import normalize_base as _normalize_base, build_chat_url
+from src.session_search import search_session_messages
 from src.prompt_security import untrusted_context_message
 from core.exceptions import SessionNotFoundError
 from src.auth_helpers import get_current_user
@@ -39,6 +40,7 @@ from routes.chat_helpers import (
    _enforce_chat_privileges,
 )
 from src.action_intents import classify_tool_intent as _classify_tool_intent
+from src.tool_policy import build_effective_tool_policy

 logger = logging.getLogger(__name__)

@@ -167,13 +169,20 @@ def _recover_empty_session_model(sess, session_id: str, owner: str | None = None
    Covers the window between endpoint setup and the first chat send: the
    picker showed a model in the dropdown but the session record never got
    written (Issue #587 — UI uses the cached endpoint list, not s.model).
-    Without this, we'd POST the upstream with model="" and get a generic
-    401/503 instead of using the model the user already picked.
-
-    Returns True iff sess.model was repaired.
+    For ChatGPT Subscription, also repairs stale OpenAI API model names such as
+    ``gpt-5`` that are not accepted by the Codex-backed ChatGPT account route.
    """
-    if getattr(sess, "model", None):
-        return False
+    current_model = (getattr(sess, "model", "") or "").strip()
+    endpoint_url = (getattr(sess, "endpoint_url", "") or "").strip()
+    is_chatgpt_subscription = False
+    if current_model:
+        try:
+            from src.chatgpt_subscription import is_chatgpt_subscription_base
+            is_chatgpt_subscription = is_chatgpt_subscription_base(endpoint_url)
+            if not is_chatgpt_subscription:
+                return False
+        except Exception:
+            return False
    db = SessionLocal()
    try:
        # Prefer the endpoint whose base URL matches the session — we know the
@@ -192,16 +201,51 @@ def _recover_empty_session_model(sess, session_id: str, owner: str | None = None
                    break
        if not ep:
            return False
+        if not is_chatgpt_subscription:
+            try:
+                from src.chatgpt_subscription import is_chatgpt_subscription_base
+                is_chatgpt_subscription = is_chatgpt_subscription_base(getattr(ep, "base_url", "") or endpoint_url)
+            except Exception:
+                is_chatgpt_subscription = False
        try:
            cached = json.loads(ep.cached_models) if isinstance(ep.cached_models, str) else (ep.cached_models or [])
        except Exception:
            cached = []
        if not cached:
+            visible = []
+        else:
+            try:
+                visible = _visible_models(cached, getattr(ep, "hidden_models", None))
+            except Exception:
+                visible = cached
+        if current_model and current_model in {str(item).strip() for item in visible}:
            return False
-        try:
-            visible = _visible_models(cached, getattr(ep, "hidden_models", None))
-        except Exception:
-            visible = cached
+        if is_chatgpt_subscription:
+            live_models = []
+            if getattr(ep, "provider_auth_id", None):
+                try:
+                    from src.chatgpt_subscription import fetch_available_models
+                    from src.endpoint_resolver import resolve_endpoint_runtime
+                    _base, api_key = resolve_endpoint_runtime(ep, owner=owner)
+                    if api_key:
+                        live_models = fetch_available_models(api_key)
+                        if live_models:
+                            ep.cached_models = json.dumps(live_models)
+                            db.commit()
+                except Exception:
+                    live_models = []
+            # ChatGPT Subscription recovery must use the live Codex catalog.
+            # Cached rows are only trusted above to avoid revalidating a model
+            # that is already present in the visible picker list.
+            cached = live_models
+            if not cached:
+                return False
+            try:
+                visible = _visible_models(cached, getattr(ep, "hidden_models", None))
+            except Exception:
+                visible = cached
+            if current_model and current_model in {str(item).strip() for item in visible}:
+                return False
        if not visible:
            return False
        model = visible[0]
@@ -211,14 +255,17 @@ def _recover_empty_session_model(sess, session_id: str, owner: str | None = None
        # Persist so the next request, websocket reconnect, or page reload
        # picks up the same model (we'd otherwise re-pick on every send
        # and silently switch on the user if the cached order shifts).
-        db_session = db.query(DBSession).filter(DBSession.id == session_id).first()
+        db_session_q = db.query(DBSession).filter(DBSession.id == session_id)
+        if owner:
+            db_session_q = db_session_q.filter(DBSession.owner == owner)
+        db_session = db_session_q.first()
        if db_session:
            db_session.model = model
            db_session.updated_at = datetime.utcnow()
            db.commit()
        sess.model = model
        logger.info(
-            "Recovered empty session model for %s — picked %r from endpoint %s",
+            "Recovered session model for %s — picked %r from endpoint %s",
            session_id, model, ep.id,
        )
        return True
@@ -304,8 +351,13 @@ def setup_chat_routes(
        # non-streaming path can't be used to bypass).
        _enforce_chat_privileges(request, sess)

+        tool_policy = build_effective_tool_policy(last_user_message=message)
+        allow_tool_preprocessing = not tool_policy.block_all_tool_calls
+
        # Inline memory command
-        memory_response = await chat_handler.handle_memory_command(sess, message)
+        memory_response = None
+        if not tool_policy.blocks("manage_memory"):
+            memory_response = await chat_handler.handle_memory_command(sess, message)
        if memory_response:
            return {"response": memory_response}

@@ -319,10 +371,15 @@ def setup_chat_routes(
            use_web=use_web,
            time_filter=time_filter,
            webhook_manager=webhook_manager,
+            allow_tool_preprocessing=allow_tool_preprocessing,
        )

        # Research injection
-        if use_research:
+        research_blocked_by_policy = (
+            tool_policy.blocks("trigger_research")
+            or tool_policy.blocks("manage_research")
+        )
+        if use_research and not research_blocked_by_policy:
            try:
                _r_ep, _r_model, _r_headers = _resolve_research_endpoint(sess)
                research_ctx = await research_handler.call_research_service(
@@ -357,6 +414,7 @@ def setup_chat_routes(
            ctx.uprefs, memory_manager, memory_vector, webhook_manager,
            character_name=ctx.preset.character_name,
            owner=ctx.user,
+            allow_background_extraction=not tool_policy.block_all_tool_calls,
        )

        return {"response": reply}
@@ -394,13 +452,22 @@ def setup_chat_routes(
        search_context = form_data.get("search_context")  # pre-fetched web search results (compare mode)
        compare_mode = str(form_data.get("compare_mode", "")).lower() == "true"
        incognito = str(form_data.get("incognito", "")).lower() == "true"
+        # Plan mode is not part of the merge-ready UI. Ignore stale clients or
+        # manual form posts that still send plan_mode=true.
+        plan_mode = False
        chat_mode = str(form_data.get("mode", "")).lower()  # 'chat' or 'agent'
-        # Workspace: confine the agent's file/shell tools to this folder. Validate
-        # it's a real directory; ignore (no confinement) otherwise.
-        workspace = (form_data.get("workspace") or "").strip()
-        if workspace:
-            _ws_real = os.path.realpath(os.path.expanduser(workspace))
-            workspace = _ws_real if os.path.isdir(_ws_real) else ""
+        workspace = ""
+        # Plan mode is a modifier on agent mode — it only makes sense with tools.
+        if plan_mode:
+            chat_mode = "agent"
+        # An approved plan being EXECUTED: the frontend sends the checklist back
+        # on each turn so we can pin it in context. This way a long plan on a
+        # weak model survives history truncation — the agent can always re-read
+        # the plan. Ignored while still proposing (plan_mode on). Capped so a
+        # huge plan can't blow the prompt.
+        approved_plan = ""
+        if not plan_mode:
+            approved_plan = (form_data.get("approved_plan") or "").strip()[:8192]
        # Did the USER explicitly pick agent mode? (vs. us auto-escalating
        # below). Skill extraction should only learn from real agent sessions,
        # not chats we quietly promoted for a notes/calendar intent.
@@ -479,11 +546,6 @@ def setup_chat_routes(
                do_research = True
                logger.info(f"Session {session} in research_pending — auto-triggering research")

-        # Persist session mode (research > agent > chat)
-        _effective_mode = 'research' if do_research else (chat_mode or 'chat')
-        if _effective_mode in ('agent', 'research', 'chat'):
-            set_session_mode(session, _effective_mode)
-
        att_ids = []
        if body and isinstance(body.get("attachments"), list):
            att_ids = [str(x) for x in body["attachments"]]
@@ -494,6 +556,10 @@ def setup_chat_routes(
                pass

        no_memory = str(form_data.get("no_memory", "")).lower() == "true"
+        pre_context_tool_policy = build_effective_tool_policy(
+            last_user_message=message,
+        )
+        allow_tool_preprocessing = not pre_context_tool_policy.block_all_tool_calls

        # Build shared context (stream path uses enhanced_message for context preface)
        ctx = await build_chat_context(
@@ -515,6 +581,7 @@ def setup_chat_routes(
            # manage_skills (agent mode). In plain chat or incognito the
            # index would be useless / unwanted noise.
            agent_mode=(chat_mode == "agent"),
+            allow_tool_preprocessing=allow_tool_preprocessing,
        )

        _research_flags = {"do": do_research}  # Mutable container for generator scope
@@ -659,6 +726,32 @@ def setup_chat_routes(
            if chat_mode == 'chat':
                disabled_tools.update({"bash", "python", "read_file", "write_file", "web_search", "web_fetch", "search_chats", "manage_tasks"})

+        # Plan mode: investigate read-only, propose a plan, don't mutate. Block
+        # every tool not on the read-only allowlist. (stream_agent_loop enforces
+        # this again + drops MCP, so this is belt-and-suspenders.)
+        if plan_mode:
+            from src.tool_security import plan_mode_disabled_tools
+            disabled_tools.update(plan_mode_disabled_tools())
+
+        tool_policy = build_effective_tool_policy(
+            disabled_tools=disabled_tools,
+            last_user_message=message,
+        )
+        disabled_tools = tool_policy.all_disabled_names()
+        research_blocked_by_policy = bool(
+            tool_policy.blocks("trigger_research")
+            or tool_policy.blocks("manage_research")
+        )
+        effective_do_research = bool(
+            do_research and _research_flags["do"] and not research_blocked_by_policy
+        )
+
+        # Persist session mode after policy/privilege gates so blocked research
+        # turns remain ordinary chat/agent streams and saved messages.
+        _effective_mode = 'research' if effective_do_research else (chat_mode or 'chat')
+        if _effective_mode in ('agent', 'research', 'chat'):
+            set_session_mode(session, _effective_mode)
+
        async def stream_with_save() -> AsyncGenerator[str, None]:
            # _effective_mode is read-only here; closure captures it from
            # the outer scope. (Was `nonlocal` but never reassigned.)
@@ -666,7 +759,7 @@ def setup_chat_routes(
            web_sources = ctx.web_sources

            # Register active stream for partial-save safety net
-            _active_streams[session] = {"status": "streaming", "partial": "", "query": message, "is_research": do_research, "mode": _effective_mode}
+            _active_streams[session] = {"status": "streaming", "partial": "", "query": message, "is_research": effective_do_research, "mode": _effective_mode}

            if ctx.preprocessed.attachment_meta:
                yield f"data: {json.dumps({'type': 'attachments', 'data': ctx.preprocessed.attachment_meta})}\n\n"
@@ -690,7 +783,7 @@ def setup_chat_routes(
                yield f"data: {json.dumps({'type': 'memories_used', 'data': ctx.used_memories})}\n\n"

            # Run research as a background task (survives page refresh)
-            if do_research and _research_flags["do"]:
+            if effective_do_research:
                _r_ep, _r_model, _r_headers = _resolve_research_endpoint(sess)
                _auth_keys = list(_r_headers.keys()) if _r_headers else []
                logger.info(f"Research endpoint resolved: model={_r_model}, endpoint={_r_ep}, auth_keys={_auth_keys}, sess_headers_keys={list(sess.headers.keys()) if isinstance(sess.headers, dict) else type(sess.headers)}")
@@ -829,7 +922,7 @@ def setup_chat_routes(
                _fallback_candidates = []

            # Send model name early so the frontend can show it during streaming
-            _model_suffix = "Research" if do_research else None
+            _model_suffix = "Research" if effective_do_research else None
            _model_info = {"type": "model_info", "model": sess.model}
            if _model_suffix:
                _model_info["suffix"] = _model_suffix
@@ -839,6 +932,12 @@ def setup_chat_routes(

            if _is_image_generation_session(sess, owner=_user):
                from src.settings import get_setting
+                if tool_policy.blocks("generate_image"):
+                    _blocked_msg = tool_policy.reason_for("generate_image")
+                    yield f'data: {json.dumps({"delta": _blocked_msg})}\n\n'
+                    yield "data: [DONE]\n\n"
+                    _active_streams.pop(session, None)
+                    return
                if not get_setting("image_gen_enabled", True):
                    yield f'data: {json.dumps({"delta": "Image generation is disabled by the administrator."})}\n\n'
                    yield "data: [DONE]\n\n"
@@ -873,6 +972,8 @@ def setup_chat_routes(
            elif chat_mode == "chat":
                _chat_start = time.time()
                _answered_by = None  # set if the selected model failed and a fallback answered
+                _requested_model = sess.model
+                _actual_model = None
                # ── Chat mode: call stream_llm directly, NO tools, NO document access ──
                try:
                    _chat_candidates = [(sess.endpoint_url, sess.model, sess.headers)] + _fallback_candidates
@@ -905,10 +1006,18 @@ def setup_chat_routes(
                                    # Selected model failed; a fallback answered.
                                    # Forward the notice and remember the real model.
                                    _answered_by = data.get("answered_by") or _answered_by
+                                    _actual_model = _actual_model or _answered_by
+                                    data["selected_model"] = data.get("selected_model") or _requested_model
                                    yield chunk
+                                elif data.get("type") == "model_actual":
+                                    _actual_model = data.get("model") or _actual_model
+                                    data["requested_model"] = _requested_model
+                                    yield f'data: {json.dumps(data)}\n\n'
                                elif data.get("type") == "usage":
                                    last_metrics = data.get("data", {})
-                                    last_metrics["model"] = _answered_by or sess.model
+                                    _reported_model = last_metrics.get("model")
+                                    last_metrics["requested_model"] = _requested_model
+                                    last_metrics["model"] = _reported_model or _actual_model or _answered_by or _requested_model
                                    if ctx.context_length and last_metrics.get("input_tokens"):
                                        pct = min(round((last_metrics["input_tokens"] / ctx.context_length) * 100, 1), 100.0)
                                        last_metrics["context_percent"] = pct
@@ -945,7 +1054,8 @@ def setup_chat_routes(
                                    "tokens_per_second": _tps,
                                    "context_percent": _ctx_pct,
                                    "context_length": ctx.context_length,
-                                    "model": sess.model,
+                                    "model": _actual_model or _answered_by or _requested_model,
+                                    "requested_model": _requested_model,
                                    "usage_source": "estimated",
                                }
                                yield f'data: {json.dumps({"type": "metrics", "data": last_metrics})}\n\n'
@@ -957,7 +1067,7 @@ def setup_chat_routes(
                                    rag_sources=ctx.rag_sources,
                                    research_sources=research_sources,
                                    used_memories=ctx.used_memories,
-                                    do_research=do_research,
+                                    do_research=effective_do_research,
                                    incognito=incognito,
                                )
                                if _saved_id:
@@ -967,14 +1077,22 @@ def setup_chat_routes(
                                    last_metrics, ctx.uprefs, memory_manager, memory_vector, webhook_manager,
                                    incognito=incognito, compare_mode=compare_mode,
                                    character_name=ctx.preset.character_name,
-                                                            owner=_user,
+                                    owner=_user,
+                                    allow_background_extraction=not tool_policy.block_all_tool_calls,
                                )
                            _stream_set(session, status="done")
                            yield chunk
                except (asyncio.CancelledError, GeneratorExit):
                    if full_response:
                        logger.info("Client disconnected mid-stream (chat mode) for session %s, saving partial (%d chars)", session, len(full_response))
-                        _stopped_content, _stopped_md = clean_thinking_for_save(full_response, {"stopped": True, "model": sess.model})
+                        _stopped_content, _stopped_md = clean_thinking_for_save(
+                            full_response,
+                            {
+                                "stopped": True,
+                                "model": _actual_model or _answered_by or _requested_model,
+                                "requested_model": _requested_model,
+                            },
+                        )
                        sess.add_message(ChatMessage("assistant", _stopped_content, metadata=_stopped_md))
                        if not incognito:
                            session_manager.save_sessions()
@@ -986,6 +1104,8 @@ def setup_chat_routes(
                _agent_rounds = 0
                _agent_tool_calls = 0
                _answered_by = None  # set if the selected model failed and a fallback answered
+                _requested_model = sess.model
+                _actual_model = None
                try:
                    from src.settings import get_setting
                    from src.agent_tools import MAX_AGENT_ROUNDS as _DEFAULT_ROUNDS
@@ -1012,9 +1132,12 @@ def setup_chat_routes(
                        active_document=active_doc,
                        session_id=session,
                        disabled_tools=disabled_tools if disabled_tools else None,
+                        tool_policy=tool_policy,
                        owner=_user,
                        fallbacks=_fallback_candidates,
-                        workspace=workspace or None,
+                        workspace=None,
+                        plan_mode=plan_mode,
+                        approved_plan=approved_plan or None,
                    ):
                        if chunk.startswith("data: ") and not chunk.startswith("data: [DONE]"):
                            try:
@@ -1035,6 +1158,8 @@ def setup_chat_routes(
                                    "doc_stream_open", "doc_stream_delta",
                                    "doc_update", "doc_suggestions", "ui_control",
                                    "rounds_exhausted",
+                                    "ask_user",
+                                    "plan_update",
                                ):
                                    if data.get("type") == "agent_step":
                                        _agent_rounds = max(_agent_rounds, data.get("round", 1))
@@ -1047,10 +1172,18 @@ def setup_chat_routes(
                                    # model so metrics reflect it, not the masked
                                    # selected model.
                                    _answered_by = data.get("answered_by") or _answered_by
+                                    _actual_model = _actual_model or _answered_by
+                                    data["selected_model"] = data.get("selected_model") or _requested_model
                                    yield chunk
+                                elif data.get("type") == "model_actual":
+                                    _actual_model = data.get("model") or _actual_model
+                                    data["requested_model"] = _requested_model
+                                    yield f'data: {json.dumps(data)}\n\n'
                                elif data.get("type") == "metrics":
                                    last_metrics = data.get("data", {})
-                                    last_metrics["model"] = _answered_by or sess.model
+                                    _reported_model = last_metrics.get("model")
+                                    last_metrics["requested_model"] = last_metrics.get("requested_model") or _requested_model
+                                    last_metrics["model"] = _reported_model or _actual_model or _answered_by or _requested_model
                                    yield f'data: {json.dumps({"type": "metrics", "data": last_metrics})}\n\n'
                            except json.JSONDecodeError:
                                yield chunk
@@ -1078,6 +1211,7 @@ def setup_chat_routes(
                                    skills_manager=skills_manager,
                                    owner=_user,
                                    extract_skills=user_requested_agent,
+                                    allow_background_extraction=not tool_policy.block_all_tool_calls,
                                )
                            _stream_set(session, status="done")
                            yield chunk
@@ -1091,7 +1225,14 @@ def setup_chat_routes(
                    try:
                        if full_response:
                            logger.info("Client disconnected mid-stream for session %s, saving partial response (%d chars)", session, len(full_response))
-                            _stopped_content2, _stopped_md2 = clean_thinking_for_save(full_response, {"stopped": True, "model": sess.model})
+                            _stopped_content2, _stopped_md2 = clean_thinking_for_save(
+                                full_response,
+                                {
+                                    "stopped": True,
+                                    "model": _actual_model or _answered_by or _requested_model,
+                                    "requested_model": _requested_model,
+                                },
+                            )
                            sess.add_message(ChatMessage("assistant", _stopped_content2, metadata=_stopped_md2))
                            if not incognito:
                                session_manager.save_sessions()
@@ -1110,11 +1251,29 @@ def setup_chat_routes(
            finally:
                _active_streams.pop(session, None)

-        # Run the stream as a DETACHED background task so it survives the client
-        # closing the tab / navigating away (true terminal-agent behavior). The
-        # SSE response just subscribes (replay buffered output + live); dropping
-        # the SSE only removes a subscriber — the run keeps going and saves the
-        # assistant message on completion regardless. Reconnect via /api/chat/resume.
+        # Compare panes are short-lived, single-shot generations whose sessions
+        # exist only to drive that one pane — there's nothing to "resume" and
+        # the user expects the pane's Stop button (which aborts the fetch,
+        # closing this SSE) to promptly cancel the upstream LLM call. Detaching
+        # them would keep burning upstream tokens/compute after the pane is
+        # stopped or the comparison is abandoned, and would surface a stale
+        # "still streaming" /resume target for a session nobody will revisit.
+        #
+        # So: stream them directly (no agent_runs wrapping). Starlette cancels
+        # the underlying async generator (raising CancelledError/GeneratorExit
+        # inside it) as soon as it notices the client disconnected — which the
+        # mode-specific except blocks above already handle by saving the
+        # partial response exactly once. This stops the upstream call promptly
+        # without waiting on the next streamed chunk.
+        #
+        # Normal chat/agent streams keep the DETACHED behavior below: they
+        # survive the client closing the tab / navigating away. The SSE response just subscribes (replay
+        # buffered output + live); dropping the SSE only removes a subscriber —
+        # the run keeps going and saves the assistant message on completion
+        # regardless. Reconnect via /api/chat/resume.
+        if compare_mode:
+            return StreamingResponse(_safe_stream(), media_type="text/event-stream")
+
        agent_runs.start(session, _safe_stream())
        return StreamingResponse(agent_runs.subscribe(session), media_type="text/event-stream")

@@ -1185,45 +1344,16 @@ def setup_chat_routes(
            return []

        _user = get_current_user(request)
-        query_term = q.strip()
-        db = SessionLocal()
-        try:
-            base_q = (
-                db.query(DBChatMessage, DBSession.name)
-                .join(DBSession, DBChatMessage.session_id == DBSession.id)
-                .filter(
-                    DBSession.archived == False,
-                    DBChatMessage.content.ilike(f"%{query_term}%"),
-                    DBChatMessage.role.in_(["user", "assistant"]),
-                )
+        return [
+            result.to_dict()
+            for result in search_session_messages(
+                q,
+                limit=limit,
+                owner=_user,
+                restrict_owner=_user is not None,
+                include_legacy_owner=False,
            )
-            if _user:
-                base_q = base_q.filter(DBSession.owner == _user)
-            rows = base_q.order_by(DBChatMessage.timestamp.desc()).limit(limit).all()
-
-            results = []
-            for msg, session_name in rows:
-                content = msg.content or ""
-                lower_content = content.lower()
-                idx = lower_content.find(query_term.lower())
-                if idx == -1:
-                    snippet = content[:120]
-                else:
-                    start = max(0, idx - 50)
-                    end = min(len(content), idx + len(query_term) + 50)
-                    snippet = ("..." if start > 0 else "") + content[start:end] + ("..." if end < len(content) else "")
-
-                results.append({
-                    "session_id": msg.session_id,
-                    "session_name": session_name or "Untitled",
-                    "role": msg.role,
-                    "content_snippet": snippet,
-                    "timestamp": msg.timestamp.isoformat() if msg.timestamp else None,
-                })
-
-            return results
-        finally:
-            db.close()
+        ]

    # ------------------------------------------------------------------ #
    # POST /api/rewrite — lightweight rewrite of last AI message (no tools)
@@ -0,0 +1,170 @@
+"""ChatGPT Subscription device-flow setup routes."""
+
+import json
+import logging
+import uuid
+from typing import Dict, Optional
+
+from fastapi import HTTPException, Request
+
+from core.database import ModelEndpoint, ProviderAuthSession, SessionLocal, utcnow_naive
+from routes.device_flow import (
+    DeviceFlowPoll,
+    DeviceFlowStart,
+    PendingDeviceFlowStore,
+    create_device_flow_router,
+)
+from src.auth_helpers import get_current_user
+from src import chatgpt_subscription
+
+logger = logging.getLogger(__name__)
+
+_DEVICE_FLOW_STORE = PendingDeviceFlowStore()
+
+
+def _provision_endpoint(tokens: Dict, owner: Optional[str]) -> Dict:
+    access_token = tokens.get("access_token")
+    refresh_token = tokens.get("refresh_token")
+    if not access_token or not refresh_token:
+        raise ValueError("ChatGPT token response was missing access_token or refresh_token")
+
+    base = chatgpt_subscription.DEFAULT_CHATGPT_SUBSCRIPTION_BASE_URL
+    models = chatgpt_subscription.fetch_available_models(access_token)
+    if not models:
+        raise ValueError("ChatGPT Subscription connected, but no usable Codex models were discovered for this account.")
+    db = SessionLocal()
+    try:
+        auth = (
+            db.query(ProviderAuthSession)
+            .filter(
+                ProviderAuthSession.provider == chatgpt_subscription.CHATGPT_SUBSCRIPTION_PROVIDER,
+                ProviderAuthSession.owner == owner,
+            )
+            .first()
+        )
+        if auth is None:
+            auth = ProviderAuthSession(
+                id=str(uuid.uuid4())[:8],
+                provider=chatgpt_subscription.CHATGPT_SUBSCRIPTION_PROVIDER,
+                owner=owner,
+                label="ChatGPT Subscription",
+                base_url=base,
+                auth_mode="chatgpt",
+            )
+            db.add(auth)
+        auth.base_url = base
+        auth.access_token = access_token
+        auth.refresh_token = refresh_token
+        auth.last_refresh = utcnow_naive()
+        auth.auth_mode = "chatgpt"
+
+        ep = (
+            db.query(ModelEndpoint)
+            .filter(
+                ModelEndpoint.base_url == base,
+                ModelEndpoint.provider_auth_id == auth.id,
+                ModelEndpoint.owner == owner,
+            )
+            .first()
+        )
+        if ep is None:
+            ep = ModelEndpoint(
+                id=str(uuid.uuid4())[:8],
+                name="ChatGPT Subscription",
+                base_url=base,
+                model_type="llm",
+                endpoint_kind="api",
+                owner=owner,
+            )
+            db.add(ep)
+        ep.name = "ChatGPT Subscription"
+        ep.base_url = base
+        ep.api_key = None
+        ep.provider_auth_id = auth.id
+        ep.is_enabled = True
+        ep.supports_tools = False
+        ep.model_type = "llm"
+        ep.endpoint_kind = "api"
+        ep.model_refresh_mode = "manual"
+        ep.cached_models = json.dumps(models)
+        db.commit()
+        result = {
+            "id": ep.id,
+            "name": ep.name,
+            "base_url": ep.base_url,
+            "models": models,
+        }
+    finally:
+        db.close()
+
+    try:
+        from routes.model_routes import _invalidate_models_cache
+
+        _invalidate_models_cache()
+    except Exception:
+        pass
+    return result
+
+
+def _start_device_flow(request: Request, _form) -> DeviceFlowStart:
+    try:
+        data = chatgpt_subscription.request_device_code()
+    except Exception as exc:
+        raise chatgpt_subscription.to_http_exception(exc)
+
+    device_auth_id = data.get("device_auth_id")
+    user_code = data.get("user_code")
+    if not device_auth_id or not user_code:
+        raise HTTPException(502, "ChatGPT did not return a complete device code")
+    verification_uri = data.get("verification_uri") or f"{chatgpt_subscription.CHATGPT_OAUTH_ISSUER}/codex/device"
+    return DeviceFlowStart(
+        pending={
+            "device_auth_id": device_auth_id,
+            "user_code": user_code,
+            "owner": get_current_user(request) or None,
+        },
+        response={
+            "user_code": user_code,
+            "verification_uri": verification_uri,
+        },
+        interval=int(data.get("interval") or 5),
+        expires_in=int(data.get("expires_in") or 900),
+    )
+
+
+def _poll_device_flow(_request: Request, pending: Dict) -> DeviceFlowPoll:
+    try:
+        data = chatgpt_subscription.poll_device_auth(pending["device_auth_id"], pending["user_code"])
+    except Exception as exc:
+        logger.debug("ChatGPT device poll failed: %s", exc)
+        return DeviceFlowPoll.pending(str(exc))
+
+    authorization_code = data.get("authorization_code")
+    code_verifier = data.get("code_verifier")
+    if authorization_code and code_verifier:
+        try:
+            tokens = chatgpt_subscription.exchange_authorization_code(authorization_code, code_verifier)
+            result = _provision_endpoint(tokens, pending["owner"])
+        except Exception as exc:
+            logger.exception("ChatGPT Subscription endpoint provisioning failed")
+            raise chatgpt_subscription.to_http_exception(exc)
+        return DeviceFlowPoll.authorized(result)
+
+    err = data.get("error") or data.get("status")
+    if err in ("authorization_pending", "pending", None):
+        return DeviceFlowPoll.pending()
+    if err == "slow_down":
+        return DeviceFlowPoll.slow_down(int(data.get("interval") or 0) or None)
+    if err in ("expired_token", "access_denied", "denied"):
+        return DeviceFlowPoll.failed(err)
+    return DeviceFlowPoll.pending(err or "unknown")
+
+
+def setup_chatgpt_subscription_routes():
+    return create_device_flow_router(
+        prefix="/api/chatgpt-subscription",
+        tags=["chatgpt-subscription"],
+        store=_DEVICE_FLOW_STORE,
+        start_flow=_start_device_flow,
+        poll_flow=_poll_device_flow,
+    )
@@ -15,10 +15,13 @@ from typing import Any
 from fastapi import APIRouter, BackgroundTasks, Body, HTTPException, Request
 from fastapi.responses import StreamingResponse

-from src.auth_helpers import require_user
+from src.auth_helpers import require_authenticated_request, require_user
 from src.tool_implementations import do_manage_notes
+from src.constants import COOKBOOK_STATE_FILE


+COOKBOOK_READ_SCOPES = {"cookbook:read", "cookbook:launch"}
+COOKBOOK_LAUNCH_SCOPES = {"cookbook:launch"}
 TODO_READ_SCOPES = {"todos:read", "todos:write"}
 TODO_WRITE_SCOPES = {"todos:write"}
 EMAIL_READ_SCOPES = {"email:read", "email:draft", "email:send"}
@@ -39,7 +42,9 @@ async def _as_owner(request: Request, owner: str, fn, *args, **kwargs):
    the scope-gated owner (not the "api" pseudo-user the bearer middleware sets).
    Restores the original value when done. Works for sync and async handlers."""
    orig = getattr(request.state, "current_user", None)
+    orig_api_token = getattr(request.state, "api_token", None)
    request.state.current_user = owner
+    request.state.api_token = False
    try:
        result = fn(*args, **kwargs)
        if asyncio.iscoroutine(result):
@@ -47,6 +52,13 @@ async def _as_owner(request: Request, owner: str, fn, *args, **kwargs):
        return result
    finally:
        request.state.current_user = orig
+        if orig_api_token is None:
+            try:
+                delattr(request.state, "api_token")
+            except AttributeError:
+                pass
+        else:
+            request.state.api_token = orig_api_token


 def _scope_owner(request: Request, allowed: set[str]) -> str:
@@ -130,6 +142,11 @@ def setup_codex_routes(
                    "actions": ["library", "read", "create", "delete"],
                    "available": documents_library_endpoint is not None,
                },
+                "cookbook": {
+                    "read": scoped(COOKBOOK_READ_SCOPES),
+                    "launch": scoped(COOKBOOK_LAUNCH_SCOPES),
+                    "actions": ["tasks", "servers", "output", "serve", "stop"],
+                },
            },
            "safety": {
                "email_send_requires_confirmation": True,
@@ -139,7 +156,7 @@ def setup_codex_routes(

    @router.get("/plugin.zip")
    def plugin_zip(request: Request):
-        require_user(request)
+        require_authenticated_request(request)
        root = Path(__file__).resolve().parent.parent / "integrations" / "codex"
        if not root.exists():
            raise HTTPException(404, "Codex plugin bundle not found")
@@ -373,6 +390,374 @@ def setup_codex_routes(
            raise HTTPException(400, f"Invalid document payload: {exc}")
        return await _as_owner(request, owner, documents_create_endpoint, request, req)

+    # ── Cookbook surface ──
+    # Lets the agent run the same launch / monitor / kill loop the user
+    # would do by hand in the Cookbook UI: read the current task list +
+    # tmux output, launch a serve task, stop one.  Two scopes:
+    #   cookbook:read   — list tasks + tail output + list servers
+    #   cookbook:launch — also start/stop serves (host shell exec)
+    # `cookbook:launch` is genuinely powerful: /api/model/serve runs SSH'd
+    # commands on the user's hosts. The existing _validate_serve_cmd
+    # allowlist (vllm/python3/sglang/llama-server/etc., no shell metachars)
+    # keeps the agent inside the same sandbox the UI uses.
+
+    async def _run_shell(cmd: str, timeout: float = 15.0) -> dict:
+        """Run a shell command, return {exit_code, stdout, stderr}."""
+        import asyncio as _asyncio
+        try:
+            proc = await _asyncio.create_subprocess_shell(
+                cmd,
+                stdout=_asyncio.subprocess.PIPE,
+                stderr=_asyncio.subprocess.PIPE,
+            )
+            try:
+                stdout_b, stderr_b = await _asyncio.wait_for(proc.communicate(), timeout=timeout)
+            except _asyncio.TimeoutError:
+                proc.kill()
+                return {"exit_code": -1, "stdout": "", "stderr": "timed out"}
+            return {
+                "exit_code": proc.returncode,
+                "stdout": stdout_b.decode(errors="replace"),
+                "stderr": stderr_b.decode(errors="replace"),
+            }
+        except Exception as exc:
+            return {"exit_code": -1, "stdout": "", "stderr": str(exc)}
+
+    def _read_cookbook_state() -> dict:
+        from pathlib import Path as _Path
+        import json as _json
+        p = _Path(COOKBOOK_STATE_FILE)
+        if not p.exists():
+            return {}
+        try:
+            return _json.loads(p.read_text(encoding="utf-8"))
+        except Exception:
+            return {}
+
+    def _redact_task(t: dict) -> dict:
+        """Strip secrets before returning to the agent."""
+        clean = {k: v for k, v in t.items() if k not in ("hf_token", "_secrets")}
+        if isinstance(clean.get("payload"), dict):
+            pl = clean["payload"]
+            clean["payload"] = {k: v for k, v in pl.items()
+                                if k not in ("hf_token", "_secrets")}
+        return clean
+
+    @router.get("/cookbook/tasks")
+    async def codex_cookbook_tasks(request: Request):
+        _scope_owner(request, COOKBOOK_READ_SCOPES)
+        state = _read_cookbook_state()
+        tasks = state.get("tasks") or []
+        return {"tasks": [_redact_task(t) for t in tasks]}
+
+    @router.get("/cookbook/servers")
+    async def codex_cookbook_servers(request: Request):
+        _scope_owner(request, COOKBOOK_READ_SCOPES)
+        state = _read_cookbook_state()
+        servers = state.get("env", {}).get("servers") or []
+        # Strip ssh creds / passwords; keep only what's needed to pick a host.
+        cleaned = []
+        for s in servers:
+            cleaned.append({
+                "name": s.get("name"),
+                "host": s.get("host"),
+                "port": s.get("port"),
+                "env": s.get("env"),
+                "envPath": s.get("envPath"),
+                "platform": s.get("platform"),
+                "modelDirs": s.get("modelDirs"),
+            })
+        return {"servers": cleaned}
+
+    @router.get("/cookbook/output/{session_id}")
+    async def codex_cookbook_output(request: Request, session_id: str, tail: int = 400):
+        _scope_owner(request, COOKBOOK_READ_SCOPES)
+        # Defensive: session_id must be the tmux-style id we issue
+        # (`serve-XXXX` / `cookbook-XXXX` / `queue-XXXX`); anything else
+        # would let the agent run arbitrary `tmux capture-pane` targets.
+        import re as _re
+        if not _re.fullmatch(r"[a-zA-Z0-9_-]+", session_id):
+            raise HTTPException(400, "Invalid session id")
+        tail = max(20, min(int(tail or 400), 4000))
+        # Resolve the task's host (if any) from cookbook state so we can
+        # ssh to the right box, exactly as the UI does in _reconnectTask.
+        state = _read_cookbook_state()
+        tasks = state.get("tasks") or []
+        task = next((t for t in tasks if t.get("sessionId") == session_id), None)
+        if task is None:
+            raise HTTPException(404, "task not found")
+        host = (task.get("remoteHost") or "").strip()
+        ssh_port = (task.get("sshPort") or "").strip()
+        # Prefer the persisted log file over the tmux pane. The pane gets
+        # overwritten by the post-crash neofetch banner + bash prompt the
+        # moment vllm exits; the log file is the raw stdout/stderr and
+        # survives unchanged. Falls back to pane for older tasks predating
+        # the tee-to-log runner change.
+        log_path = f"/tmp/odysseus-tmux/{session_id}.log"
+        inner = (
+            f"if [ -s {log_path} ]; then tail -n {tail} {log_path}; "
+            f"else tmux capture-pane -t {session_id} -p -S -{tail}; fi"
+        )
+        if host:
+            port_flag = f"-p {ssh_port} " if ssh_port and ssh_port != "22" else ""
+            import shlex
+            cmd = f"ssh {port_flag}{host} {shlex.quote(inner)}"
+        else:
+            cmd = inner
+        result = await _run_shell(cmd, timeout=15)
+        return {
+            "session_id": session_id,
+            "host": host or "local",
+            "exit_code": result.get("exit_code"),
+            "output": result.get("stdout", ""),
+            "task": _redact_task(task),
+        }
+
+    @router.post("/cookbook/serve")
+    async def codex_cookbook_serve(request: Request, body: dict[str, Any] = Body(default_factory=dict)):
+        _scope_owner(request, COOKBOOK_LAUNCH_SCOPES)
+        # Wraps /api/model/serve with the SAME validation the UI uses.
+        # _validate_serve_cmd (called inside model_serve) rejects shell
+        # metachars and requires the leading binary to be in the
+        # cookbook allowlist (vllm / python3 / sglang / llama-server / ...).
+        from routes.cookbook_helpers import ServeRequest
+        # Accept friendly aliases agents naturally reach for. Without these,
+        # passing `host` silently maps to nothing and the serve runs LOCAL
+        # instead of on the intended remote — exactly the bug an agent
+        # would never debug on its own.
+        norm = dict(body or {})
+        if "host" in norm and "remote_host" not in norm:
+            norm["remote_host"] = norm.pop("host")
+        if "model" in norm and "repo_id" not in norm:
+            norm["repo_id"] = norm.pop("model")
+        if "ssh_port" not in norm and "port" in norm and (str(norm.get("port") or "").isdigit() and int(norm["port"]) >= 1000):
+            # Heuristic: if `port` looks like an SSH port (≥1000) and there's
+            # no explicit ssh_port, treat it as such. UI ports (8000, 8001,
+            # 30000) belong inside the cmd string, not here.
+            pass  # leave as-is — user's `port` here is ambiguous; skip remap.
+        try:
+            req = ServeRequest(**norm)
+        except Exception as exc:
+            raise HTTPException(400, f"Invalid serve payload: {exc}")
+        serve_endpoint = _find_endpoint(None, "POST", "/api/model/serve")
+        # Fall back to importing from the cookbook router registered on app.
+        if serve_endpoint is None:
+            from fastapi import FastAPI
+            app: FastAPI = request.app
+            for route in app.routes:
+                if getattr(route, "path", None) == "/api/model/serve" and "POST" in getattr(route, "methods", set()):
+                    serve_endpoint = route.endpoint
+                    break
+        if serve_endpoint is None:
+            raise HTTPException(503, "model serve endpoint unavailable")
+        return await serve_endpoint(request, req)
+
+    @router.post("/cookbook/stop/{session_id}")
+    async def codex_cookbook_stop(request: Request, session_id: str):
+        _scope_owner(request, COOKBOOK_LAUNCH_SCOPES)
+        import re as _re
+        if not _re.fullmatch(r"[a-zA-Z0-9_-]+", session_id):
+            raise HTTPException(400, "Invalid session id")
+        state = _read_cookbook_state()
+        tasks = state.get("tasks") or []
+        task = next((t for t in tasks if t.get("sessionId") == session_id), None)
+        host = ((task or {}).get("remoteHost") or "").strip()
+        ssh_port = ((task or {}).get("sshPort") or "").strip()
+        if host:
+            port_flag = f"-p {ssh_port} " if ssh_port and ssh_port != "22" else ""
+            cmd = f"ssh {port_flag}{host} \"tmux kill-session -t {session_id}\""
+        else:
+            cmd = f"tmux kill-session -t {session_id}"
+        result = await _run_shell(cmd, timeout=10)
+        return {"session_id": session_id, "exit_code": result.get("exit_code"), "host": host or "local"}
+
+    @router.get("/cookbook/cached")
+    async def codex_cookbook_cached(request: Request, host: str | None = None):
+        """List cached models on a configured server (or local if host is omitted).
+        Mirrors `list_cached_models` from the chat agent so external agents have
+        the same inventory view before deciding what to serve/download."""
+        _scope_owner(request, COOKBOOK_READ_SCOPES)
+        # Hit /api/model/cached internally, with the same modelDirs the chat
+        # agent's list_cached_models would resolve from cookbook state.
+        state = _read_cookbook_state()
+        env = state.get("env") if isinstance(state, dict) else {}
+        servers = (env.get("servers") if isinstance(env, dict) else None) or []
+        HF_DEFAULTS = {"~/.cache/huggingface/hub", "~/.cache/huggingface"}
+        def _dirs_for(srv: dict) -> str:
+            mds = srv.get("modelDirs") if isinstance(srv, dict) else None
+            if isinstance(mds, list):
+                extras = [d for d in mds if isinstance(d, str) and d.strip() and d.strip() not in HF_DEFAULTS]
+                return ",".join(extras)
+            if isinstance(mds, str) and mds.strip() not in HF_DEFAULTS:
+                return mds
+            return ""
+        # Resolve friendly host name → real host (matches list_cached_models flow).
+        resolved_host = host or ""
+        srv: dict[str, Any] = {}
+        if host:
+            srv = next(
+                (s for s in servers if isinstance(s, dict)
+                 and (s.get("name") == host or s.get("host") == host)),
+                {},
+            )
+            if srv and srv.get("host"):
+                resolved_host = srv["host"]
+        else:
+            srv = next((s for s in servers if isinstance(s, dict) and not (s.get("host") or "").strip()), {})
+        params: dict[str, str] = {}
+        if resolved_host:
+            params["host"] = resolved_host
+        md = _dirs_for(srv)
+        if md:
+            params["model_dir"] = md
+        if srv.get("port"):
+            params["ssh_port"] = str(srv["port"])
+        if srv.get("platform"):
+            params["platform"] = srv["platform"]
+        cached_endpoint = _find_endpoint(None, "GET", "/api/model/cached")
+        if cached_endpoint is None:
+            from fastapi import FastAPI
+            app: FastAPI = request.app
+            for route in app.routes:
+                if getattr(route, "path", None) == "/api/model/cached" and "GET" in getattr(route, "methods", set()):
+                    cached_endpoint = route.endpoint
+                    break
+        if cached_endpoint is None:
+            raise HTTPException(503, "model cached endpoint unavailable")
+        # The endpoint reads host/model_dir/ssh_port/platform as kwargs.
+        return await cached_endpoint(
+            request,
+            host=params.get("host") or None,
+            model_dir=params.get("model_dir") or None,
+            ssh_port=params.get("ssh_port") or None,
+            platform=params.get("platform") or None,
+        )
+
+    @router.get("/cookbook/presets")
+    async def codex_cookbook_presets(request: Request):
+        """List saved serve presets (model + host + port + launch cmd).
+        Counterpart to `list_serve_presets`. Use BEFORE composing a `serve`
+        body — the user's saved preset usually has the working cmd already."""
+        _scope_owner(request, COOKBOOK_READ_SCOPES)
+        state = _read_cookbook_state()
+        presets = state.get("presets") or []
+        out = []
+        for p in presets:
+            if not isinstance(p, dict):
+                continue
+            out.append({
+                "name": p.get("name"),
+                "model": p.get("model") or p.get("modelId"),
+                "host": p.get("host") or p.get("remoteHost"),
+                "port": p.get("port"),
+                "cmd": p.get("cmd"),
+            })
+        return {"presets": out, "default_host": (state.get("env") or {}).get("defaultServer", "")}
+
+    @router.post("/cookbook/preset/{name}")
+    async def codex_cookbook_serve_preset(request: Request, name: str):
+        """Launch a saved preset by name. Reuses the working cmd + host the
+        user already saved, avoiding the cmd-allowlist trial-and-error loop."""
+        _scope_owner(request, COOKBOOK_LAUNCH_SCOPES)
+        import re as _re
+        if not _re.fullmatch(r"[A-Za-z0-9 _.:@\-]+", name):
+            raise HTTPException(400, "Invalid preset name")
+        state = _read_cookbook_state()
+        presets = state.get("presets") or []
+        lname = name.lower().strip()
+        chosen = next(
+            (p for p in presets if isinstance(p, dict) and (p.get("name") or "").lower() == lname),
+            None,
+        )
+        if chosen is None:
+            chosen = next(
+                (p for p in presets if isinstance(p, dict) and lname in (p.get("name") or "").lower()),
+                None,
+            )
+        if chosen is None:
+            raise HTTPException(404, f"No preset matching {name!r}")
+        repo_id = chosen.get("model") or chosen.get("modelId") or ""
+        cmd = (chosen.get("cmd") or "").strip()
+        host = chosen.get("host") or chosen.get("remoteHost") or ""
+        if not repo_id or not cmd or cmd.startswith("(adopted"):
+            raise HTTPException(400, f"Preset {chosen.get('name')!r} has no launchable cmd "
+                                     "(adopted from external launch). Use POST /cookbook/serve "
+                                     "with the actual cmd instead.")
+        # Reuse the serve handler we already validated.
+        from routes.cookbook_helpers import ServeRequest
+        body = {"repo_id": repo_id, "cmd": cmd}
+        if host:
+            body["remote_host"] = host
+        try:
+            req = ServeRequest(**body)
+        except Exception as exc:
+            raise HTTPException(400, f"Preset payload invalid: {exc}")
+        serve_endpoint = _find_endpoint(None, "POST", "/api/model/serve")
+        if serve_endpoint is None:
+            from fastapi import FastAPI
+            app: FastAPI = request.app
+            for route in app.routes:
+                if getattr(route, "path", None) == "/api/model/serve" and "POST" in getattr(route, "methods", set()):
+                    serve_endpoint = route.endpoint
+                    break
+        if serve_endpoint is None:
+            raise HTTPException(503, "model serve endpoint unavailable")
+        return await serve_endpoint(request, req)
+
+    @router.post("/cookbook/adopt")
+    async def codex_cookbook_adopt(request: Request, body: dict[str, Any] = Body(default_factory=dict)):
+        """Adopt an existing tmux session (one started via raw ssh+tmux) into
+        cookbook tracking. Needed when serve_model rejects a cmd and the
+        agent falls back to direct ssh — without adoption the session is
+        invisible to the UI. Body: {tmux_session, model, host?, port?}."""
+        _scope_owner(request, COOKBOOK_LAUNCH_SCOPES)
+        norm = dict(body or {})
+        sess = (norm.get("tmux_session") or norm.get("session_id") or "").strip()
+        model = (norm.get("model") or norm.get("repo_id") or "").strip()
+        host = (norm.get("host") or norm.get("remote_host") or "").strip()
+        port = norm.get("port") or 8000
+        import re as _re
+        if not sess or not _re.fullmatch(r"[a-zA-Z0-9_-]+", sess):
+            raise HTTPException(400, "tmux_session required, [a-zA-Z0-9_-]+ only")
+        if not model:
+            raise HTTPException(400, "model required")
+        # Verify the tmux session exists on the target host before adopting.
+        import shlex
+        if host:
+            check = f"ssh {shlex.quote(host)} 'tmux has-session -t {shlex.quote(sess)}'"
+        else:
+            check = f"tmux has-session -t {shlex.quote(sess)}"
+        chk = await _run_shell(check, timeout=8)
+        if chk.get("exit_code") not in (0, None):
+            raise HTTPException(404, f"tmux session {sess!r} not found on {host or 'local'}")
+        # Write into cookbook_state.json.
+        import time as _t, json as _json
+        from core.atomic_io import atomic_write_json
+        from pathlib import Path as _Path
+        cookbook_state_path = _Path(COOKBOOK_STATE_FILE)
+        try:
+            state = _json.loads(cookbook_state_path.read_text(encoding="utf-8"))
+        except Exception:
+            state = {}
+        tasks = state.setdefault("tasks", [])
+        if any(isinstance(t, dict) and t.get("sessionId") == sess for t in tasks):
+            return {"ok": True, "already_tracked": True, "session_id": sess}
+        tasks.append({
+            "id": sess, "sessionId": sess,
+            "name": model.split("/")[-1] if "/" in model else model,
+            "type": "serve", "status": "running",
+            "output": f"Adopted externally-launched session {sess!r} on {host or 'local'}.",
+            "ts": int(_t.time() * 1000),
+            "payload": {"repo_id": model, "remote_host": host, "_cmd": "(adopted — launched outside cookbook)", "port": int(port)},
+            "remoteHost": host, "sshPort": "", "platform": "linux",
+            "_serveReady": False, "_endpointAdded": False, "_adoptedExternally": True,
+        })
+        try:
+            atomic_write_json(cookbook_state_path, state)
+        except Exception as exc:
+            raise HTTPException(500, f"state write failed: {exc}")
+        return {"ok": True, "session_id": sess, "host": host or "local"}
+
    return router


@@ -387,7 +772,7 @@ def setup_claude_routes() -> APIRouter:

    @router.get("/plugin.zip")
    def plugin_zip(request: Request):
-        require_user(request)
+        require_authenticated_request(request)
        # Only ship the skills/ subtree so extracting at ~/.claude/ doesn't dump
        # README.md or other bundle metadata into the user's claude config dir.
        skills_root = Path(__file__).resolve().parent.parent / "integrations" / "claude" / "skills"
@@ -12,6 +12,7 @@ import logging
 from core.database import Comparison, SessionLocal
 from core.session_manager import SessionManager
 from src.auth_helpers import get_current_user
+from routes.session_routes import _reject_raw_endpoint_url_for_non_admin

 logger = logging.getLogger(__name__)

@@ -38,6 +39,24 @@ def _owned_endpoint_by_url(db, base_url, owner):
    return owner_filter(q, ModelEndpoint, owner).first()


+def _owned_endpoint_by_id(db, endpoint_id, owner):
+    """ModelEndpoint whose id == `endpoint_id` and is VISIBLE to `owner` (their
+    own rows + legacy null-owner "shared" rows); None otherwise.
+
+    Preferred over _owned_endpoint_by_url for credential resolution: two visible
+    endpoints can share the same base_url but hold DIFFERENT api_keys (e.g. two
+    accounts on the same provider). A base_url-only match returns whichever row
+    sorts first, so it can copy the WRONG owner-scoped key into the [CMP] session.
+    An id pins the exact registered endpoint, so /api/compare/start prefers it and
+    only falls back to URL matching for legacy / admin raw-URL callers. Owner
+    scoping is identical to _owned_endpoint_by_url (a null/empty owner is a no-op).
+    """
+    from core.database import ModelEndpoint
+    from src.auth_helpers import owner_filter
+    q = db.query(ModelEndpoint).filter(ModelEndpoint.id == endpoint_id)
+    return owner_filter(q, ModelEndpoint, owner).first()
+
+
 class RecordVoteRequest(BaseModel):
    prompt: str
    models: List[str]
@@ -54,8 +73,10 @@ def setup_compare_routes(session_manager: SessionManager):
        prompt: str = Form(...),
        model_a: str = Form(...),
        model_b: str = Form(...),
-        endpoint_a: str = Form(...),
-        endpoint_b: str = Form(...),
+        endpoint_a: str = Form(""),
+        endpoint_b: str = Form(""),
+        endpoint_a_id: str = Form(""),
+        endpoint_b_id: str = Form(""),
        is_blind: str = Form("true"),
    ):
        """Create two ephemeral sessions and a comparison record.
@@ -63,10 +84,10 @@ def setup_compare_routes(session_manager: SessionManager):
        Returns the comparison ID and the two session IDs so the client
        can fire two independent SSE streams to /api/chat_stream.
        """
+        user = getattr(request.state, 'current_user', None)
        comp_id = str(uuid.uuid4())
        sid_a = str(uuid.uuid4())
        sid_b = str(uuid.uuid4())
-        user = getattr(request.state, 'current_user', None)

        # Blind mapping: randomly assign left/right
        blind = str(is_blind).lower() == "true"
@@ -87,31 +108,94 @@ def setup_compare_routes(session_manager: SessionManager):
        # de-anonymizing the comparison before the user votes (issue #1285).
        slot_name = {session_left: "Model A", session_right: "Model B"}

-        # Create ephemeral sessions (prefixed [CMP])
-        for sid, model, endpoint in [(sid_a, model_a, endpoint_a), (sid_b, model_b, endpoint_b)]:
+        # SECURITY: resolve and validate BOTH endpoints before creating any
+        # session. Compare copies a registered endpoint's Authorization header
+        # into the [CMP] session, so validating one endpoint while creating its
+        # session, then rejecting the other, would leave a partial compare
+        # session behind with that header attached. Doing all the owner-scope
+        # resolution + raw-URL rejection up front means a 403 on either endpoint
+        # aborts the whole request with nothing created and no header copied.
+        from src.endpoint_resolver import build_chat_url, build_headers, normalize_base
+        resolved = []
+        db = SessionLocal()
+        try:
+            for sid, model, endpoint, endpoint_id in [
+                (sid_a, model_a, endpoint_a, endpoint_a_id),
+                (sid_b, model_b, endpoint_b, endpoint_b_id),
+            ]:
+                # Prefer an explicit endpoint id: it pins the EXACT registered
+                # endpoint (and its api_key), even when two endpoints visible to
+                # the caller share a base_url with different keys — a URL-only
+                # match would copy whichever row sorts first, i.e. possibly the
+                # wrong key. Fall back to URL resolution only for legacy / admin
+                # raw-URL callers that don't send an id.
+                eid = endpoint_id.strip() if isinstance(endpoint_id, str) else ""
+                if eid:
+                    ep = _owned_endpoint_by_id(db, eid, user)
+                    if ep is None:
+                        # An id the caller can't see (wrong owner / deleted) must
+                        # NOT silently fall back to a same-URL row with a different
+                        # key — that's exactly the mix-up ids exist to prevent.
+                        raise HTTPException(404, "Model endpoint not found")
+                    # The id already resolved the endpoint; ignore any raw URL the
+                    # caller also sent and dial the stored config instead.
+                    endpoint = ep.base_url
+                elif not endpoint:
+                    raise HTTPException(
+                        422, "endpoint_a/endpoint_b or endpoint_a_id/endpoint_b_id is required"
+                    )
+                else:
+                    # Resolve the supplied URL to a ModelEndpoint the caller owns
+                    # (their own rows + legacy null-owner shared rows), scoped so a
+                    # comparison can't borrow another user's private endpoint key.
+                    base = normalize_base(endpoint)
+                    ep = _owned_endpoint_by_url(db, base, user)
+                # Reject *unregistered* raw URLs for signed-in non-admins; a
+                # matched registered endpoint supplies an id so the caller can
+                # still compare endpoints they own. Blanket-rejecting here (the
+                # earlier `endpoint_id=None` call) locked non-admins out of
+                # compare entirely, since compare resolves endpoints by URL with
+                # no endpoint_id. Mirrors the gallery inpaint/harmonize checks.
+                # Raised here (phase 1), before any session exists.
+                _reject_raw_endpoint_url_for_non_admin(
+                    request, user, str(ep.id) if ep is not None else None, endpoint
+                )
+                # Bind the [CMP] session to the RESOLVED endpoint, not the raw
+                # caller-supplied string. When the URL matches a registered
+                # endpoint visible to the caller, use that row's own normalized
+                # base URL (the same value owner scoping + endpoint validation
+                # already vetted) so the session dials exactly where the stored
+                # config points. The raw `endpoint` only survives for callers
+                # allowed to pass one — admins / single-user mode, where
+                # `_reject_raw_endpoint_url_for_non_admin` is a no-op and `ep`
+                # is None. Mirrors the registered-endpoint path in session_routes.
+                session_endpoint_url = (
+                    build_chat_url(normalize_base(ep.base_url)) if ep is not None else endpoint
+                )
+                # Headers come only from a matched endpoint's key; None when
+                # `ep` is None (raw admin URL or no match), so a comparison can
+                # never inherit another user's key/headers.
+                headers = build_headers(ep.api_key, ep.base_url) if (ep and ep.api_key) else None
+                resolved.append((sid, model, session_endpoint_url, headers))
+        finally:
+            db.close()
+
+        # Both endpoints validated — only now create the ephemeral [CMP]
+        # sessions and copy any resolved headers.
+        for sid, model, session_endpoint_url, headers in resolved:
            name = f"[CMP] {slot_name[sid]}" if blind else f"[CMP] {model.split('/')[-1]}"
            session_manager.create_session(
                session_id=sid,
                name=name,
-                endpoint_url=endpoint,
+                endpoint_url=session_endpoint_url,
                model=model,
                rag=False,
                owner=user,
            )
-            # Copy API key from endpoint config
-            db = SessionLocal()
-            try:
-                from src.endpoint_resolver import build_headers, normalize_base
-                # Find matching endpoint by URL, scoped to the caller so a
-                # comparison can't borrow another user's private endpoint key.
-                base = normalize_base(endpoint)
-                ep = _owned_endpoint_by_url(db, base, user)
-                if ep and ep.api_key:
-                    s = session_manager.sessions.get(sid)
-                    if s:
-                        s.headers = build_headers(ep.api_key, ep.base_url)
-            finally:
-                db.close()
+            if headers:
+                s = session_manager.sessions.get(sid)
+                if s:
+                    s.headers = headers

        # Store comparison record
        db = SessionLocal()
@@ -121,8 +205,12 @@ def setup_compare_routes(session_manager: SessionManager):
                prompt=prompt,
                model_a=model_a,
                model_b=model_b,
-                endpoint_a=endpoint_a,
-                endpoint_b=endpoint_b,
+                # Record the URL the session actually dials. For URL callers this
+                # is their raw input; for id-only callers (empty endpoint_a/_b)
+                # fall back to the resolved endpoint URL so the column stays
+                # meaningful and non-null. resolved is in [a, b] order.
+                endpoint_a=endpoint_a or resolved[0][2],
+                endpoint_b=endpoint_b or resolved[1][2],
                is_blind=blind,
                blind_mapping=json.dumps(mapping),
                owner=user,
@@ -11,20 +11,24 @@ import uuid
 import json
 import csv
 import io
+import os
 import httpx
 from pathlib import Path
 from datetime import datetime
-from fastapi import APIRouter, Query, Depends, Response
+from urllib.parse import urljoin, urlparse, urlunparse
+
+from fastapi import APIRouter, Query, Depends, Response, HTTPException
 from typing import List, Dict, Optional

-from src.auth_helpers import require_user
 from core.middleware import require_admin
+from src.url_safety import check_outbound_url

 logger = logging.getLogger(__name__)

-DATA_DIR = Path(__file__).resolve().parent.parent / "data"
-SETTINGS_FILE = DATA_DIR / "settings.json"
-LOCAL_CONTACTS_FILE = DATA_DIR / "contacts.json"
+from src.constants import DATA_DIR as _DATA_DIR, SETTINGS_FILE as _SETTINGS_FILE, CONTACTS_FILE as _CONTACTS_FILE
+DATA_DIR = Path(_DATA_DIR)
+SETTINGS_FILE = Path(_SETTINGS_FILE)
+LOCAL_CONTACTS_FILE = Path(_CONTACTS_FILE)


 def _load_settings():
@@ -53,6 +57,21 @@ def _carddav_configured(cfg: Optional[Dict] = None) -> bool:
    return bool((cfg.get("url") or "").strip())


+def _validate_carddav_url(url: str) -> str:
+    cleaned = (url if isinstance(url, str) else "").strip().rstrip("/")
+    ok, reason = check_outbound_url(
+        cleaned,
+        block_private=os.getenv("CARDDAV_BLOCK_PRIVATE_IPS", "false").lower() == "true",
+    )
+    if not ok:
+        raise ValueError(f"Rejected CardDAV URL: {reason}")
+    return cleaned
+
+
+def _carddav_base_url(cfg: Dict) -> str:
+    return _validate_carddav_url(cfg.get("url") or "")
+
+
 def _normalize_contact(contact: Dict) -> Dict:
    emails = []
    for e in contact.get("emails") or ([] if not contact.get("email") else [contact.get("email")]):
@@ -219,14 +238,18 @@ _contact_cache = {"contacts": [], "fetched_at": None}
 def _abs_url(href: str) -> str:
    """Combine a multistatus <href> (an absolute path like
    /user/contacts/x.vcf) with the configured CardDAV server origin so we
-    get a fully-qualified URL to PUT/DELETE. If href is already absolute
-    (http...), return it as-is."""
-    from urllib.parse import urlparse, urlunparse
-    if href.startswith("http://") or href.startswith("https://"):
-        return href
+    get a fully-qualified URL to PUT/DELETE. Absolute hrefs are accepted only
+    for the configured origin; a cross-origin href is treated as a path on the
+    configured server so a malicious CardDAV response cannot redirect later
+    writes/deletes to cloud metadata or another host."""
    cfg = _get_carddav_config()
-    p = urlparse(cfg["url"])
-    return urlunparse((p.scheme, p.netloc, href, "", "", ""))
+    base = _carddav_base_url(cfg)
+    base_p = urlparse(base)
+    joined = urljoin(base.rstrip("/") + "/", href or "")
+    joined_p = urlparse(joined)
+    if (joined_p.scheme, joined_p.netloc) != (base_p.scheme, base_p.netloc):
+        joined = urlunparse((base_p.scheme, base_p.netloc, joined_p.path or "/", "", joined_p.query, ""))
+    return _validate_carddav_url(joined)


 # CardDAV REPORT body — pull every card's etag + raw vCard in ONE request,
@@ -297,6 +320,7 @@ def _fetch_contacts(force=False):
        return contacts

    try:
+        cfg["url"] = _carddav_base_url(cfg)
        auth = None
        if cfg["username"]:
            auth = (cfg["username"], cfg["password"])
@@ -353,8 +377,8 @@ def _create_contact(name: str, email: str) -> bool:

    contact_uid = str(uuid.uuid4())
    vcard = _build_vcard(name, email, contact_uid)
-    url = cfg["url"].rstrip("/") + "/" + contact_uid + ".vcf"
    try:
+        url = _carddav_base_url(cfg) + "/" + contact_uid + ".vcf"
        auth = None
        if cfg["username"]:
            auth = (cfg["username"], cfg["password"])
@@ -382,7 +406,7 @@ def _vcard_url(uid: str) -> str:
    escape the collection and target an arbitrary CardDAV resource."""
    from urllib.parse import quote
    cfg = _get_carddav_config()
-    return cfg["url"].rstrip("/") + "/" + quote(uid, safe="") + ".vcf"
+    return _carddav_base_url(cfg) + "/" + quote(uid, safe="") + ".vcf"


 def _import_vcards(text: str) -> Dict:
@@ -413,6 +437,11 @@ def _import_vcards(text: str) -> Dict:
        if imported:
            _save_local_contacts(contacts)
        return {"imported": imported, "failed": 0, "total": len(parsed)}
+    try:
+        base_url = _carddav_base_url(cfg)
+    except ValueError as e:
+        logger.warning("CardDAV import URL rejected: %s", e)
+        return {"imported": 0, "failed": 0, "total": 0, "error": str(e)}
    auth = (cfg["username"], cfg["password"]) if cfg["username"] else None
    # Split into individual cards. re.split drops the BEGIN line, so we
    # re-add it. Normalize CRLF.
@@ -441,7 +470,7 @@ def _import_vcards(text: str) -> Dict:
        elif not re.search(r"^VERSION:", block, re.MULTILINE):
            block = block.replace("BEGIN:VCARD", "BEGIN:VCARD\nVERSION:4.0", 1)
        vcard = block.replace("\n", "\r\n") + "\r\n"
-        url = cfg["url"].rstrip("/") + "/" + quote(uid, safe="") + ".vcf"
+        url = base_url + "/" + quote(uid, safe="") + ".vcf"
        try:
            r = httpx.put(
                url, data=vcard.encode("utf-8"),
@@ -601,8 +630,8 @@ def _update_contact(uid: str, name: str, emails: List[str], phones: List[str]) -
    vcard = _build_vcard(name, "", uid=uid, emails=emails, phones=phones)
    # Use the real resource href (handles externally-created contacts whose
    # filename != UID); falls back to the <uid>.vcf guess.
-    url = _resolve_resource_url(uid)
    try:
+        url = _resolve_resource_url(uid)
        auth = (cfg["username"], cfg["password"]) if cfg["username"] else None
        r = httpx.put(
            url,
@@ -630,8 +659,8 @@ def _delete_contact(uid: str) -> bool:
        _save_local_contacts(remaining)
        return True

-    url = _resolve_resource_url(uid)
    try:
+        url = _resolve_resource_url(uid)
        auth = (cfg["username"], cfg["password"]) if cfg["username"] else None
        r = httpx.delete(url, auth=auth, timeout=10)
        if r.status_code in (200, 204):
@@ -747,7 +776,13 @@ def setup_contacts_routes():
        settings = _load_settings()
        for key in ("carddav_url", "carddav_username", "carddav_password"):
            if key in data:
-                settings[key] = data[key]
+                if key == "carddav_url" and str(data[key] or "").strip():
+                    try:
+                        settings[key] = _validate_carddav_url(data[key])
+                    except ValueError as e:
+                        raise HTTPException(400, str(e))
+                else:
+                    settings[key] = data[key]
        _save_settings(settings)
        # Force re-fetch
        _contact_cache["fetched_at"] = None
@@ -11,6 +11,8 @@ import shlex
 from fastapi import HTTPException
 from pydantic import BaseModel

+from core.platform_compat import _ssh_exec_argv
+
 logger = logging.getLogger(__name__)


@@ -28,8 +30,9 @@ _LOCAL_MODEL_ID_RE = re.compile(r"^[A-Za-z0-9][A-Za-z0-9._-]*$")
 _OLLAMA_MODEL_ID_RE = re.compile(r"^[A-Za-z0-9][A-Za-z0-9._:/-]{0,200}$")
 # Include pattern is a glob: allow typical safe glyphs only.
 _INCLUDE_RE = re.compile(r"^[A-Za-z0-9._\-*?/\[\]]+$")
-# Remote host: user@host (optionally with :port-free hostname parts).
-_REMOTE_HOST_RE = re.compile(r"^[A-Za-z0-9._-]+@[A-Za-z0-9._-]+$")
+# Remote host: either `user@host` or plain `host` (alias is allowed), where host
+# is a safe DNS-like token or a short SSH config alias.
+_REMOTE_HOST_RE = re.compile(r"^(?:[A-Za-z0-9._-]+@)?[A-Za-z0-9._-]+$")
 # HF tokens and API tokens are url-safe base64-like.
 _TOKEN_RE = re.compile(r"^[A-Za-z0-9._~+/=-]+$")
 # Session IDs we mint look like "cookbook-deadbeef" or "serve-deadbeef".
@@ -79,7 +82,7 @@ def _validate_remote_host(v: str | None) -> str | None:
    if v is None or v == "":
        return None
    if not _REMOTE_HOST_RE.match(v):
-        raise HTTPException(400, "Invalid remote_host — must be user@host, no SSH option syntax")
+        raise HTTPException(400, "Invalid remote_host — must be host or user@host, no SSH option syntax")
    return v


@@ -195,6 +198,20 @@ def _pip_install_attempt(pip_cmd: str) -> str:
    )


+def _pip_command(python_cmd: str) -> str:
+    """Return a pip command for either a pip executable or a Python executable."""
+    cmd = python_cmd.strip()
+    if " -m pip" in cmd or cmd in {"pip", "pip3"}:
+        return python_cmd
+    if cmd in {"python", "python3", "python.exe"} or cmd.endswith(("/python", "/python3", "\\python.exe")):
+        return f"{python_cmd} -m pip"
+    return python_cmd
+
+
+def _pip_break_system_packages_check(pip_cmd: str) -> str:
+    return f"{pip_cmd} install --help 2>/dev/null | grep -q -- --break-system-packages"
+
+
 def _pip_install_fallback_chain(package: str, *, python_cmd: str = "python3 -m pip", upgrade: bool = False) -> str:
    """Build a bash pip install fallback chain that surfaces errors.

@@ -206,33 +223,44 @@ def _pip_install_fallback_chain(package: str, *, python_cmd: str = "python3 -m p
    exit code is preserved (no ``| tail`` masking) and the last 5 lines of
    pip output appear in the Cookbook log on failure.
    """
+    from core.platform_compat import IS_WINDOWS
    upgrade_flag = " -U" if upgrade else ""
    # Shell-quote the package spec: an extras spec like ``llama-cpp-python[server]``
    # contains brackets that bash would treat as a glob, so it must be quoted
    # before being embedded in the install command. Plain names (e.g.
    # ``huggingface_hub``) are returned unchanged by ``shlex.quote``.
    pkg = shlex.quote(package)
-    base = _pip_install_attempt(f"{python_cmd} install -q{upgrade_flag} {pkg}")
-    user = _pip_install_attempt(f"{python_cmd} install --user --break-system-packages -q{upgrade_flag} {pkg}")
+    # llama-cpp-python source builds are brittle on older distro pip/packaging
+    # stacks (common on WSL images). Prefer the prebuilt wheel index whenever
+    # this package is requested so dependency-install tasks are reliable.
+    if "llama-cpp-python" in package:
+        pkg += " --extra-index-url https://abetlen.github.io/llama-cpp-python/whl/cpu"
+
+    pip_cmd = _pip_command(python_cmd)
+    base = _pip_install_attempt(f"{pip_cmd} install -q{upgrade_flag} {pkg}")
+    user = _pip_install_attempt(f"{pip_cmd} install --user -q{upgrade_flag} {pkg}")
+    user_break_system = _pip_install_attempt(f"{pip_cmd} install --user --break-system-packages -q{upgrade_flag} {pkg}")
+    user_fallback = f"( {user} || {{ {_pip_break_system_packages_check(pip_cmd)} && {user_break_system}; }} )"
    # Derive the python executable for the venv detection check.
    # Must use the same interpreter that pip belongs to; hardcoding
    # python3 breaks when pip lives in a venv that only has "python".
-    if " -m pip" in python_cmd:
-        python_exe = python_cmd.replace(" -m pip", "")
-    elif python_cmd.strip() == "pip":
+    if " -m pip" in pip_cmd:
+        python_exe = pip_cmd.replace(" -m pip", "")
+    elif pip_cmd.strip() == "pip":
        python_exe = "python"
-    elif python_cmd.strip() == "pip3":
+    elif pip_cmd.strip() == "pip3":
        python_exe = "python3"
    else:
        python_exe = "python3"
    venv_check = f'{python_exe} -c "import sys; sys.exit(0 if sys.prefix != sys.base_prefix else 1)"'
-    # Negated: `! venv_check` succeeds (exit 0) when NOT in a venv → `&&` tries
-    # --user.  When IN a venv `! venv_check` fails → `&&` skips --user and the
+    # Negated: `! venv_check` succeeds (exit 0) when NOT in a venv -> `&&` tries
+    # --user. When IN a venv `! venv_check` fails -> `&&` skips --user and the
    # group exits non-zero, propagating the base-install failure instead of
    # masking it as success (the `|| { venv_check || … }` shape from #903
    # swallowed the exit code because venv_check's exit-0 became the group's
-    # result).
-    return f"{base} || {{ ! {venv_check} && {user}; }}"
+    # result). `--break-system-packages` is only attempted when the active pip
+    # supports it; older pip versions abort with "no such option" otherwise.
+    return f"{base} || {{ ! {venv_check} && {user_fallback}; }}"


 def _venv_safe_local_pip_install_cmd(cmd: str, *, local: bool, in_venv: bool) -> str:
@@ -263,6 +291,55 @@ def _venv_safe_local_pip_install_cmd(cmd: str, *, local: bool, in_venv: bool) ->
    return shlex.join(stripped)


+def _pip_install_command_without_break_system_packages(cmd: str) -> str:
+    try:
+        parts = shlex.split(cmd)
+    except ValueError:
+        return cmd
+    stripped = [part for part in parts if part != "--break-system-packages"]
+    return shlex.join(stripped)
+
+
+def _pip_install_help_check_from_cmd(cmd: str) -> str | None:
+    try:
+        parts = shlex.split(cmd)
+    except ValueError:
+        return None
+    try:
+        install_index = parts.index("install")
+    except ValueError:
+        return None
+    if install_index <= 0:
+        return None
+    pip_prefix = parts[:install_index]
+    return f"{shlex.join(pip_prefix + ['install', '--help'])} 2>/dev/null | grep -q -- --break-system-packages"
+
+
+def _append_pip_install_runner_lines(runner_lines: list[str], cmd: str) -> None:
+    """Append a pip install command, guarding --break-system-packages support.
+
+    The Dependencies UI may submit ``python3 -m pip install --user
+    --break-system-packages ...`` for non-venv installs. That flag is useful on
+    PEP-668-locked distros, but older pip (including Ubuntu 22.04's apt pip in
+    the NVIDIA CUDA base image) aborts with "no such option". Branch at runner
+    time so stale browser JS and remote targets are handled by the server too.
+    """
+    if "--break-system-packages" not in (cmd or ""):
+        runner_lines.append(cmd)
+        return
+    help_check = _pip_install_help_check_from_cmd(cmd)
+    without_break = _pip_install_command_without_break_system_packages(cmd)
+    if not help_check or without_break == cmd:
+        runner_lines.append(cmd)
+        return
+    runner_lines.append(f"if {help_check}; then")
+    runner_lines.append(f"  {cmd}")
+    runner_lines.append("else")
+    runner_lines.append('  echo "[odysseus] pip does not support --break-system-packages; installing without it."')
+    runner_lines.append(f"  {without_break}")
+    runner_lines.append("fi")
+
+
 def _user_shell_path_bootstrap() -> list[str]:
    return [
        'ODYSSEUS_USER_SHELL="${SHELL:-}"',
@@ -271,11 +348,14 @@ def _user_shell_path_bootstrap() -> list[str]:
        '  if [ -n "$ODYSSEUS_USER_PATH" ]; then export PATH="$ODYSSEUS_USER_PATH:$PATH"; fi',
        'fi',
        'command -v python3 >/dev/null 2>&1 || python3() { python "$@"; }',
+        'command -v python >/dev/null 2>&1 || python() { python3 "$@"; }',
    ]


-def _cached_model_scan_script(model_dirs: list[str] | None = None) -> str:
-    """Build the standalone Python scanner used by /api/model/cached."""
+def _cached_model_scan_script(model_dirs: list[str] | None = None, add_hf_cache: str | None = None) -> str:
+    """Build the standalone Python scanner used by /api/model/cached.
+    Allows for an additional HuggingFace cache path to be scanned (i.e. Windows HF cache for local WSL envs.)
+    """
    lines = [
        "import json, os, re, shutil, subprocess, urllib.request",
        "models = []",
@@ -338,6 +418,15 @@ def _cached_model_scan_script(model_dirs: list[str] | None = None) -> str:
        "                if f.is_file(): nf += 1; sz += f.stat().st_size",
        "                if f.name.endswith('.incomplete'): ic = True",
        "        snap = os.path.join(cache, d, 'snapshots')",
+        "        # Windows HF cache stores files directly in snapshots/; blobs/ may be empty.",
+        "        # Fallback: scan snapshots for real files when blobs yielded nothing.",
+        "        if sz == 0 and os.path.isdir(snap):",
+        "            for sd in os.listdir(snap):",
+        "                sf = os.path.join(snap, sd)",
+        "                if not os.path.isdir(sf): continue",
+        "                for f in os.scandir(sf):",
+        "                    if f.is_file(): nf += 1; sz += f.stat().st_size",
+        "                    if f.name.endswith('.incomplete'): ic = True",
        "        is_diffusion = False; gguf_files = []",
        "        if os.path.isdir(snap):",
        "            for sd in os.listdir(snap):",
@@ -346,6 +435,21 @@ def _cached_model_scan_script(model_dirs: list[str] | None = None) -> str:
        "                if os.path.exists(os.path.join(sf, 'model_index.json')): is_diffusion = True",
        "                for f in collect_ggufs(sf): f['rel_path'] = sd + '/' + f['rel_path']; gguf_files.append(f)",
        "        models.append({'repo_id':rid,'size_bytes':sz,'nb_files':nf,'has_incomplete':ic,'path':cache,'is_diffusion':is_diffusion,'is_gguf':bool(gguf_files),'gguf_files':gguf_files})",
+        "def hf_cache_paths():",
+        "    candidates = []",
+        "    def add(p):",
+        "        if not p: return",
+        "        p = os.path.expanduser(p)",
+        "        if p not in candidates: candidates.append(p)",
+        "    add(os.environ.get('HUGGINGFACE_HUB_CACHE'))",
+        "    hf_home = os.environ.get('HF_HOME')",
+        "    if hf_home: add(os.path.join(hf_home, 'hub'))",
+        "    add('~/.cache/huggingface/hub')",
+        "    # Docker images mount ./data/huggingface at /app/.cache/huggingface.",
+        "    # When HOME is /root, expanduser() misses that persisted cache.",
+        "    add('/app/.cache/huggingface/hub')",
+        f"    add({add_hf_cache!r})" if add_hf_cache else "",
+        "    return candidates",
        "def scan_dir(p):",
        "    if not os.path.isdir(p) or not safe_path(p): return",
        "    for d in sorted(os.listdir(p)):",
@@ -409,7 +513,7 @@ def _cached_model_scan_script(model_dirs: list[str] | None = None) -> str:
        "            seen.add(name)",
        "            models.append({'repo_id':name,'size_bytes':size_bytes,'nb_files':1,'has_incomplete':False,'path':'ollama','backend':'ollama','is_ollama':True})",
        "        return",
-        "scan_hf(os.path.expanduser('~/.cache/huggingface/hub'))",
+        "for _hf_cache in hf_cache_paths(): scan_hf(_hf_cache)",
        "scan_ollama()",
        "scan_ollama_api()",
    ]
@@ -525,6 +629,7 @@ def _validate_serve_cmd(v: str | None) -> str | None:
    # Backticks and raw newlines are never legitimate here.
    if any(c in v for c in ("`", "\n", "\r")):
        raise HTTPException(400, "Invalid characters in cmd")
+
    # Known GGUF launcher prelude → validate the serve invocation(s) it guards.
    m = _GGUF_PRELUDE_RE.match(v)
    if m:
@@ -533,9 +638,19 @@ def _validate_serve_cmd(v: str | None) -> str | None:
        for part in rest.split("||"):
            _check_serve_binary(part.strip())
        return v
+
    # Otherwise: a single invocation — no shell metacharacters allowed.
+    # Temporarily replace safe $(printf %s ...) expressions with a placeholder
+    # to avoid triggering the metacharacter/command-injection checks.
+    cleaned_v = v
+    printf_matches = list(re.finditer(r"\$\(\s*printf\s+%s\s+([^\n()]*?)\)", v))
+    for match in printf_matches:
+        inner = match.group(1)
+        if not any(c in inner for c in (";", "&&", "||", "$(", "`")):
+            cleaned_v = cleaned_v.replace(match.group(0), "/placeholder/safe/path.gguf")
+
    # (`$(` was the original intent; bare `$` is fine for shell-safe paths.)
-    if any(c in v for c in (";", "&&", "||", "$(")):
+    if any(c in cleaned_v for c in (";", "&&", "||", "$(")):
        raise HTTPException(400, "Invalid characters in cmd")
    _check_serve_binary(v)
    return v
@@ -546,12 +661,34 @@ def _append_serve_preflight_exit_lines(runner_lines: list[str], *, keep_shell_op
    runner_lines.append('if [ -n "$ODYSSEUS_PREFLIGHT_EXIT" ]; then')
    runner_lines.append('  echo ""; echo "=== Process exited with code $ODYSSEUS_PREFLIGHT_EXIT ==="')
    if keep_shell_open:
+        # Decouple the post-crash interactive shell from the persistent log
+        # file. fds 3/4 were saved BEFORE the tee redirect at the top of
+        # the runner; restoring them here means the neofetch banner the
+        # user's .zshrc prints lands on the tmux pane only, not in the
+        # log file the agent's tail_serve_output reads.
+        runner_lines.append('  exec 1>&3 2>&4 3>&- 4>&- 2>/dev/null || true')
+        runner_lines.append('  sleep 0.2  # let tee child flush + exit')
        runner_lines.append('  exec "${SHELL:-/bin/bash}"')
    else:
        runner_lines.append('  exit "$ODYSSEUS_PREFLIGHT_EXIT"')
    runner_lines.append('fi')


+def _append_vllm_linux_preflight_lines(runner_lines: list[str]) -> None:
+    """Append Linux vLLM readiness lines that identify the runtime being used."""
+    # Keep the user install bin visible for Odysseus-managed `pip install --user`
+    # installs, but then report the actual CLI path so external runtimes are clear.
+    runner_lines.append('export PATH="$HOME/.local/bin:$PATH"')
+    runner_lines.append('ODYSSEUS_VLLM_BIN="$(command -v vllm 2>/dev/null || true)"')
+    runner_lines.append('if [ -z "$ODYSSEUS_VLLM_BIN" ]; then')
+    runner_lines.append('  echo "ERROR: vLLM is not installed."')
+    runner_lines.append('  ODYSSEUS_PREFLIGHT_EXIT=127')
+    runner_lines.append('else')
+    runner_lines.append('  echo "[odysseus] vLLM CLI: $ODYSSEUS_VLLM_BIN"')
+    runner_lines.append('  ODYSSEUS_VLLM_VERSION="$("$ODYSSEUS_VLLM_BIN" --version 2>&1 | head -n 1 || true)"')
+    runner_lines.append('  if [ -n "$ODYSSEUS_VLLM_VERSION" ]; then echo "[odysseus] vLLM version: $ODYSSEUS_VLLM_VERSION"; fi')
+    runner_lines.append('fi')
+
 def _append_serve_exit_code_lines(
    runner_lines: list[str],
    *,
@@ -563,7 +700,11 @@ def _append_serve_exit_code_lines(
    if is_pip_install:
        runner_lines.append('if [ $ODYSSEUS_CMD_EXIT -eq 0 ]; then echo ""; echo "DOWNLOAD_OK"; fi')
    if keep_shell_open:
-        runner_lines.append('echo ""; echo "=== Process exited with code $ODYSSEUS_CMD_EXIT ==="; exec "${SHELL:-/bin/bash}"')
+        runner_lines.append('echo ""; echo "=== Process exited with code $ODYSSEUS_CMD_EXIT ==="')
+        # See preflight branch above for the rationale on restoring fds 3/4.
+        runner_lines.append('exec 1>&3 2>&4 3>&- 4>&- 2>/dev/null || true')
+        runner_lines.append('sleep 0.2  # let tee child flush + exit')
+        runner_lines.append('exec "${SHELL:-/bin/bash}"')
    else:
        runner_lines.append('echo ""; echo "=== Process exited with code $ODYSSEUS_CMD_EXIT ==="')
        runner_lines.append('exit "$ODYSSEUS_CMD_EXIT"')
@@ -647,6 +788,7 @@ def _llama_cpp_rebuild_cmd() -> str:

 class ModelDownloadRequest(BaseModel):
    repo_id: str
+    backend: str | None = None  # "hf" (default) or "ollama"
    include: str | None = None  # glob pattern e.g. "*Q4_K_M*"
    hf_token: str | None = None
    env_prefix: str | None = None  # e.g. "source ~/venv/bin/activate"
@@ -793,3 +935,172 @@ def _ssh_ps(host, script_path, port=None):

 # Windows session dir — stored in user's temp on the remote
 WIN_SESSION_DIR = "$env:TEMP\\\\odysseus-sessions"
+
+
+def _diagnose_serve_output(text: str) -> dict | None:
+    """Server-side mirror of the Cookbook UI's common serve diagnoses.
+
+    The browser uses cookbook-diagnosis.js for clickable fixes. This gives
+    the agent/tool path the same structured signal so it can retry with an
+    adjusted command instead of guessing from raw tmux output.
+    """
+    if not text:
+        return None
+    tail = text[-6000:]
+    patterns = [
+        (
+            r"No available memory for the cache blocks|Available KV cache memory:.*-",
+            "No GPU memory left for KV cache after loading model.",
+            [
+                {"label": "retry with GPU memory utilization 0.95", "op": "replace", "flag": "--gpu-memory-utilization", "value": "0.95"},
+                {"label": "retry with context 2048", "op": "replace", "flag": "--max-model-len", "value": "2048"},
+            ],
+        ),
+        (
+            r"CUDA out of memory|torch\.cuda\.OutOfMemoryError|CUDA error: out of memory|warming up sampler|max_num_seqs.*gpu_memory_utilization",
+            "GPU ran out of memory during startup or warmup.",
+            [
+                {"label": "retry with context 4096", "op": "replace", "flag": "--max-model-len", "value": "4096"},
+                {"label": "retry with GPU memory utilization 0.80", "op": "replace", "flag": "--gpu-memory-utilization", "value": "0.80"},
+                {"label": "retry with --enforce-eager", "op": "append", "arg": "--enforce-eager"},
+            ],
+        ),
+        (
+            r"not divisib|must be divisible|attention heads.*divisible",
+            "Tensor parallel size is incompatible with the model.",
+            [
+                {"label": "retry with tensor parallel size 1", "op": "replace", "flag": "--tensor-parallel-size", "value": "1"},
+                {"label": "retry with tensor parallel size 2", "op": "replace", "flag": "--tensor-parallel-size", "value": "2"},
+            ],
+        ),
+        (
+            r"KV cache.*too (small|large)|max_model_len.*exceeds|maximum.*context",
+            "Context length is too large for available GPU memory.",
+            [
+                {"label": "retry with context 8192", "op": "replace", "flag": "--max-model-len", "value": "8192"},
+                {"label": "retry with context 4096", "op": "replace", "flag": "--max-model-len", "value": "4096"},
+            ],
+        ),
+        (
+            r"enable-auto-tool-choice requires --tool-call-parser",
+            "Auto tool choice requires an explicit tool call parser.",
+            [{"label": "retry with Hermes tool parser", "op": "append", "arg": "--tool-call-parser hermes"}],
+        ),
+        (
+            r"Please pass.*trust.remote.code=True|contains custom code which must be executed to correctly load|does not recognize this architecture|model type.*but Transformers does not",
+            "Model requires custom code or newer model support.",
+            [{"label": "retry with --trust-remote-code", "op": "append", "arg": "--trust-remote-code"}],
+        ),
+        (
+            r"There is no module or parameter named ['\"]lm_head\.input_scale['\"]|lm_head\.input_scale|weight_scale_2",
+            "vLLM cannot load this ModelOpt LM-head quantized checkpoint with the current runtime.",
+            [
+                {
+                    "label": "upgrade vLLM through the environment that provides this CLI, or use a compatible checkpoint",
+                    "op": "manual",
+                }
+            ],
+        ),
+        (
+            r"Either a revision or a version must be specified|transformers\.integrations\.hub_kernels|kernels/layer",
+            "vLLM/Transformers kernel package mismatch.",
+            [{"label": "update vLLM, Transformers, and kernels on this server", "op": "dependency", "package": "vllm transformers kernels"}],
+        ),
+        (
+            r"Address already in use|bind.*address.*in use",
+            "Port is already in use.",
+            [{"label": "retry on port 8001", "op": "replace", "flag": "--port", "value": "8001"}],
+        ),
+        (
+            r"No CUDA GPUs are available|no GPU.*found|CUDA_VISIBLE_DEVICES.*invalid",
+            "No GPUs are visible to the serve process.",
+            [{"label": "clear Cookbook GPU selection or choose available GPUs", "op": "settings", "field": "gpus", "value": ""}],
+        ),
+        (
+            r"Failed to infer device type|NVML Shared Library Not Found|No module named 'amdsmi'|platform is not available",
+            "vLLM could not find a supported GPU (CUDA or ROCm). "
+            "This machine may have integrated or unsupported graphics only.",
+            [
+                {"label": "switch to llama.cpp (CPU/Metal, works without a discrete GPU)", "op": "manual"},
+                {"label": "switch to Ollama (CPU/Metal, works without a discrete GPU)", "op": "manual"},
+            ],
+        ),
+        (
+            r"vllm.*command not found|No module named vllm|ERROR: vLLM is not installed",
+            "vLLM is not installed or not in PATH on this server.",
+            [{"label": "install vLLM in Cookbook Dependencies", "op": "dependency", "package": "vllm"}],
+        ),
+        (
+            r"sglang.*command not found|No module named sglang|SGLang is not installed",
+            "SGLang is not installed or not in PATH on this server.",
+            [{"label": "install SGLang in Cookbook Dependencies", "op": "dependency", "package": "sglang[all]"}],
+        ),
+        (
+            r"llama-server.*command not found|llama\.cpp.*not found|No module named.*llama_cpp|No module named 'starlette_context'|git: command not found|cmake: command not found",
+            "llama.cpp / llama-cpp-python dependencies are missing.",
+            [{"label": "install llama.cpp dependencies or llama-cpp-python[server]", "op": "dependency", "package": "llama-cpp-python[server]"}],
+        ),
+        (
+            r"No GGUF found on this host|no \.gguf file|No GGUF file found",
+            "No GGUF file found for this model on this host. The llama.cpp backend needs a .gguf file.",
+            [{"label": "download a GGUF build of this model (repo name usually ends in -GGUF, file like Q4_K_M.gguf)", "op": "manual"}],
+        ),
+        (
+            r"No module named 'torch'|No module named torch|No module named 'diffusers'|No module named diffusers",
+            "Diffusion serving requires PyTorch and diffusers.",
+            [{"label": "install diffusers[torch] in Cookbook Dependencies", "op": "dependency", "package": "diffusers[torch]"}],
+        ),
+        (
+            r"403 Forbidden|401 Unauthorized|Access to model.*is restricted|gated repo|not in the authorized list|awaiting a review",
+            "Model access is gated or unauthorized.",
+            [{"label": "set HF token and request model access on HuggingFace", "op": "manual"}],
+        ),
+    ]
+    for pattern, message, suggestions in patterns:
+        if re.search(pattern, tail, re.I):
+            return {"message": message, "suggestions": suggestions}
+    if re.search(r"Traceback \(most recent call last\)", tail, re.I) and not re.search(
+        r"Application startup complete|GET /v1/|Uvicorn running on", tail, re.I
+    ):
+        return {
+            "message": "Python traceback detected during serve startup.",
+            "suggestions": [{"label": "inspect traceback and retry with adjusted backend/settings", "op": "manual"}],
+        }
+    return None
+
+
+async def run_ssh_command_async(
+    remote: str,
+    ssh_port: str | None,
+    remote_cmd: str,
+    *,
+    timeout: float,
+    connect_timeout: int | None = None,
+    strict_host_key_checking: bool | None = None,
+    stdin_data: bytes | None = None,
+) -> tuple[int, bytes, bytes]:
+    """Run an ssh command with centralized timeout and stderr/stdout capture.
+    Async version of core.platform_compat.run_ssh_command_sync.
+    """
+    import asyncio
+    proc = await asyncio.create_subprocess_exec(
+        *_ssh_exec_argv(
+            remote,
+            ssh_port,
+            remote_cmd=remote_cmd,
+            connect_timeout=connect_timeout,
+            strict_host_key_checking=strict_host_key_checking,
+        ),
+        stdin=asyncio.subprocess.PIPE if stdin_data is not None else None,
+        stdout=asyncio.subprocess.PIPE,
+        stderr=asyncio.subprocess.PIPE,
+    )
+    try:
+        stdout, stderr = await asyncio.wait_for(
+            proc.communicate(input=stdin_data), timeout=timeout
+        )
+    except asyncio.TimeoutError:
+        proc.kill()
+        await proc.communicate()
+        raise
+    return proc.returncode or 0, stdout, stderr
@@ -20,39 +20,26 @@ All routes are admin-gated (endpoint/provider management is an admin action).
 """

 import json
-import time
 import uuid
 import logging
-import threading
 from typing import Dict, Optional

 import httpx
-from fastapi import APIRouter, Request, Form, HTTPException
+from fastapi import HTTPException, Request

 from core.database import SessionLocal, ModelEndpoint
-from core.middleware import require_admin
+from routes.device_flow import (
+    DeviceFlowPoll,
+    DeviceFlowStart,
+    PendingDeviceFlowStore,
+    create_device_flow_router,
+)
 from src.auth_helpers import get_current_user
 from src import copilot

 logger = logging.getLogger(__name__)

-# Pending device-flow logins, keyed by an opaque poll_id. The device_code is a
-# bearer-like secret, so it lives here (server memory) rather than in the
-# browser. Entries expire with the GitHub device code.
-#
-# NOTE: this is per-process state. The device flow assumes a single worker
-# (Odysseus' default): with multiple uvicorn workers, the poll request can land
-# on a worker that never saw the start, returning "Unknown or expired login
-# session". Move this to a shared store (DB/Redis) if running multi-worker.
-_PENDING: Dict[str, Dict] = {}
-_PENDING_LOCK = threading.Lock()
-
-
-def _prune_expired() -> None:
-    now = time.time()
-    with _PENDING_LOCK:
-        for k in [k for k, v in _PENDING.items() if v.get("expires_at", 0) < now]:
-            _PENDING.pop(k, None)
+_DEVICE_FLOW_STORE = PendingDeviceFlowStore()


 def _provision_endpoint(token: str, base: str, owner: Optional[str]) -> Dict:
@@ -112,112 +99,75 @@ def _provision_endpoint(token: str, base: str, owner: Optional[str]) -> Dict:
    return result


-def setup_copilot_routes() -> APIRouter:
-    router = APIRouter(prefix="/api/copilot", tags=["copilot"])
+def _start_device_flow(request: Request, form) -> DeviceFlowStart:
+    host = copilot.GITHUB_HOST
+    ent = str(form.get("enterprise_url") or "").strip()
+    if ent:
+        host = copilot.normalize_domain(ent)
+    try:
+        data = copilot.request_device_code(host)
+    except httpx.HTTPStatusError as e:
+        status = e.response.status_code if e.response is not None else "unknown"
+        raise HTTPException(502, f"GitHub device-code request failed (HTTP {status})")
+    except Exception as e:
+        raise HTTPException(502, f"GitHub device-code request failed: {e}")

-    @router.post("/device/start")
-    def device_start(request: Request, enterprise_url: str = Form("")):
-        require_admin(request)
-        _prune_expired()
-        host = copilot.GITHUB_HOST
-        ent = (enterprise_url or "").strip()
-        if ent:
-            host = copilot.normalize_domain(ent)
-        try:
-            data = copilot.request_device_code(host)
-        except httpx.HTTPStatusError as e:
-            status = e.response.status_code if e.response is not None else "unknown"
-            raise HTTPException(502, f"GitHub device-code request failed (HTTP {status})")
-        except Exception as e:
-            raise HTTPException(502, f"GitHub device-code request failed: {e}")
+    device_code = data.get("device_code")
+    if not device_code:
+        raise HTTPException(502, "GitHub did not return a device code")

-        device_code = data.get("device_code")
-        if not device_code:
-            raise HTTPException(502, "GitHub did not return a device code")
-        interval = int(data.get("interval") or 5)
-        expires_in = int(data.get("expires_in") or 900)
-        poll_id = uuid.uuid4().hex
-        with _PENDING_LOCK:
-            _PENDING[poll_id] = {
-                "device_code": device_code,
-                "host": host,
-                "enterprise_url": ent,
-                "interval": interval,
-                "owner": get_current_user(request) or None,
-                "expires_at": time.time() + expires_in,
-                "next_poll_at": 0.0,
-            }
-        # verification_uri_complete embeds the user code, so the browser tab we
-        # open lands the user straight on GitHub's "Authorize" screen with the
-        # code pre-filled — one click, no manual code entry.
-        return {
-            "poll_id": poll_id,
+    # verification_uri_complete embeds the user code, so the browser tab we
+    # open lands the user straight on GitHub's "Authorize" screen with the
+    # code pre-filled — one click, no manual code entry.
+    return DeviceFlowStart(
+        pending={
+            "device_code": device_code,
+            "host": host,
+            "enterprise_url": ent,
+            "owner": get_current_user(request) or None,
+        },
+        response={
            "user_code": data.get("user_code"),
            "verification_uri": data.get("verification_uri"),
            "verification_uri_complete": data.get("verification_uri_complete"),
-            "interval": interval,
-            "expires_in": expires_in,
-        }
+        },
+        interval=int(data.get("interval") or 5),
+        expires_in=int(data.get("expires_in") or 900),
+    )

-    @router.post("/device/poll")
-    def device_poll(request: Request, poll_id: str = Form(...)):
-        require_admin(request)
-        _prune_expired()
-        with _PENDING_LOCK:
-            pending = _PENDING.get(poll_id)
-        if not pending:
-            raise HTTPException(404, "Unknown or expired login session")

-        # Enforce GitHub's polling interval server-side so a chatty client
-        # can't trip slow_down.
-        now = time.time()
-        if now < pending.get("next_poll_at", 0):
-            return {"status": "pending"}
+def _poll_device_flow(_request: Request, pending: Dict) -> DeviceFlowPoll:
+    try:
+        data = copilot.poll_access_token(pending["host"], pending["device_code"])
+    except Exception as e:
+        return DeviceFlowPoll.pending(f"poll error: {e}")

+    token = data.get("access_token")
+    if token:
+        base = copilot.enterprise_base(pending["enterprise_url"]) if pending["enterprise_url"] else copilot.COPILOT_BASE
        try:
-            data = copilot.poll_access_token(pending["host"], pending["device_code"])
+            result = _provision_endpoint(token, base, pending["owner"])
        except Exception as e:
-            return {"status": "pending", "detail": f"poll error: {e}"}
+            logger.exception("Copilot endpoint provisioning failed")
+            raise HTTPException(500, f"Login succeeded but provisioning failed: {e}")
+        return DeviceFlowPoll.authorized(result)

-        token = data.get("access_token")
-        if token:
-            base = copilot.enterprise_base(pending["enterprise_url"]) if pending["enterprise_url"] else copilot.COPILOT_BASE
-            try:
-                result = _provision_endpoint(token, base, pending["owner"])
-            except Exception as e:
-                logger.exception("Copilot endpoint provisioning failed")
-                with _PENDING_LOCK:
-                    _PENDING.pop(poll_id, None)
-                raise HTTPException(500, f"Login succeeded but provisioning failed: {e}")
-            with _PENDING_LOCK:
-                _PENDING.pop(poll_id, None)
-            return {"status": "authorized", "endpoint": result}
+    err = data.get("error")
+    if err == "authorization_pending":
+        return DeviceFlowPoll.pending()
+    if err == "slow_down":
+        return DeviceFlowPoll.slow_down(int(data.get("interval") or 0) or None)
+    if err in ("expired_token", "access_denied"):
+        return DeviceFlowPoll.failed(err)
+    # Unknown error — surface but keep the session for another try.
+    return DeviceFlowPoll.pending(err or "unknown")

-        err = data.get("error")
-        if err == "authorization_pending":
-            with _PENDING_LOCK:
-                if poll_id in _PENDING:
-                    _PENDING[poll_id]["next_poll_at"] = now + pending["interval"]
-            return {"status": "pending"}
-        if err == "slow_down":
-            new_interval = int(data.get("interval") or (pending["interval"] + 5))
-            with _PENDING_LOCK:
-                if poll_id in _PENDING:
-                    _PENDING[poll_id]["interval"] = new_interval
-                    _PENDING[poll_id]["next_poll_at"] = now + new_interval
-            return {"status": "pending"}
-        if err in ("expired_token", "access_denied"):
-            with _PENDING_LOCK:
-                _PENDING.pop(poll_id, None)
-            return {"status": "failed", "error": err}
-        # Unknown error — surface but keep the session for another try.
-        return {"status": "pending", "detail": err or "unknown"}

-    @router.post("/device/cancel")
-    def device_cancel(request: Request, poll_id: str = Form(...)):
-        require_admin(request)
-        with _PENDING_LOCK:
-            _PENDING.pop(poll_id, None)
-        return {"status": "cancelled"}
-
-    return router
+def setup_copilot_routes():
+    return create_device_flow_router(
+        prefix="/api/copilot",
+        tags=["copilot"],
+        store=_DEVICE_FLOW_STORE,
+        start_flow=_start_device_flow,
+        poll_flow=_poll_device_flow,
+    )
@@ -0,0 +1,193 @@
+"""Shared OAuth/device-flow route scaffolding for provider setup."""
+
+from __future__ import annotations
+
+import inspect
+import threading
+import time
+import uuid
+from dataclasses import dataclass
+from typing import Any, Callable, Iterable, Mapping, Optional
+
+from fastapi import APIRouter, Form, HTTPException, Request
+
+from core.middleware import require_admin
+
+
+@dataclass(frozen=True)
+class DeviceFlowStart:
+    """Provider-specific start result consumed by the shared route wrapper."""
+
+    pending: Mapping[str, Any]
+    response: Mapping[str, Any]
+    interval: int = 5
+    expires_in: int = 900
+
+
+@dataclass(frozen=True)
+class DeviceFlowPoll:
+    """Normalized provider poll outcome."""
+
+    status: str
+    endpoint: Optional[Mapping[str, Any]] = None
+    error: Optional[str] = None
+    detail: Optional[str] = None
+    interval: Optional[int] = None
+
+    @classmethod
+    def pending(cls, detail: Optional[str] = None) -> "DeviceFlowPoll":
+        return cls(status="pending", detail=detail)
+
+    @classmethod
+    def slow_down(cls, interval: Optional[int] = None, detail: Optional[str] = None) -> "DeviceFlowPoll":
+        return cls(status="slow_down", interval=interval, detail=detail)
+
+    @classmethod
+    def authorized(cls, endpoint: Mapping[str, Any]) -> "DeviceFlowPoll":
+        return cls(status="authorized", endpoint=endpoint)
+
+    @classmethod
+    def failed(cls, error: str) -> "DeviceFlowPoll":
+        return cls(status="failed", error=error)
+
+
+class PendingDeviceFlowStore:
+    """Thread-safe in-memory pending device-flow store.
+
+    Device codes and provider-side secrets stay inside this process. Each entry
+    stores provider payload separately from poll metadata so provider callbacks
+    only receive the fields they created.
+    """
+
+    def __init__(self, *, time_func: Callable[[], float] = time.time):
+        self._pending: dict[str, dict[str, Any]] = {}
+        self._lock = threading.Lock()
+        self._time = time_func
+
+    def _now(self) -> float:
+        return float(self._time())
+
+    def prune_expired(self) -> None:
+        now = self._now()
+        with self._lock:
+            for key in [k for k, v in self._pending.items() if v.get("expires_at", 0) < now]:
+                self._pending.pop(key, None)
+
+    def add(self, payload: Mapping[str, Any], *, interval: int, expires_in: int) -> str:
+        self.prune_expired()
+        poll_id = uuid.uuid4().hex
+        with self._lock:
+            self._pending[poll_id] = {
+                "payload": dict(payload),
+                "interval": max(int(interval or 5), 1),
+                "expires_at": self._now() + max(int(expires_in or 900), 1),
+                "next_poll_at": 0.0,
+            }
+        return poll_id
+
+    def get_payload(self, poll_id: str) -> Optional[dict[str, Any]]:
+        self.prune_expired()
+        with self._lock:
+            entry = self._pending.get(poll_id)
+            if entry is None:
+                return None
+            return dict(entry.get("payload") or {})
+
+    def is_throttled(self, poll_id: str) -> bool:
+        with self._lock:
+            entry = self._pending.get(poll_id)
+            return bool(entry and self._now() < float(entry.get("next_poll_at") or 0))
+
+    def schedule_next(self, poll_id: str) -> None:
+        now = self._now()
+        with self._lock:
+            entry = self._pending.get(poll_id)
+            if entry is not None:
+                entry["next_poll_at"] = now + int(entry.get("interval") or 5)
+
+    def slow_down(self, poll_id: str, interval: Optional[int] = None) -> None:
+        now = self._now()
+        with self._lock:
+            entry = self._pending.get(poll_id)
+            if entry is not None:
+                new_interval = int(interval or (int(entry.get("interval") or 5) + 5))
+                entry["interval"] = max(new_interval, 1)
+                entry["next_poll_at"] = now + entry["interval"]
+
+    def pop(self, poll_id: str) -> None:
+        with self._lock:
+            self._pending.pop(poll_id, None)
+
+
+async def _maybe_await(value: Any) -> Any:
+    if inspect.isawaitable(value):
+        return await value
+    return value
+
+
+def _pending_response(detail: Optional[str] = None) -> dict[str, Any]:
+    response: dict[str, Any] = {"status": "pending"}
+    if detail:
+        response["detail"] = detail
+    return response
+
+
+def create_device_flow_router(
+    *,
+    prefix: str,
+    tags: Iterable[str],
+    store: PendingDeviceFlowStore,
+    start_flow: Callable[[Request, Mapping[str, Any]], DeviceFlowStart],
+    poll_flow: Callable[[Request, Mapping[str, Any]], DeviceFlowPoll],
+) -> APIRouter:
+    """Create standard `/device/start|poll|cancel` routes for a provider."""
+
+    router = APIRouter(prefix=prefix, tags=list(tags))
+
+    @router.post("/device/start")
+    async def device_start(request: Request):
+        require_admin(request)
+        form = await request.form()
+        start = await _maybe_await(start_flow(request, form))
+        interval = int(start.interval or 5)
+        expires_in = int(start.expires_in or 900)
+        poll_id = store.add(start.pending, interval=interval, expires_in=expires_in)
+        response = dict(start.response)
+        response.update({"poll_id": poll_id, "interval": interval, "expires_in": expires_in})
+        return response
+
+    @router.post("/device/poll")
+    async def device_poll(request: Request, poll_id: str = Form(...)):
+        require_admin(request)
+        payload = store.get_payload(poll_id)
+        if payload is None:
+            raise HTTPException(404, "Unknown or expired login session")
+        if store.is_throttled(poll_id):
+            return {"status": "pending"}
+
+        try:
+            outcome = await _maybe_await(poll_flow(request, payload))
+        except Exception:
+            store.pop(poll_id)
+            raise
+
+        if outcome.status == "authorized":
+            store.pop(poll_id)
+            return {"status": "authorized", "endpoint": dict(outcome.endpoint or {})}
+        if outcome.status == "failed":
+            store.pop(poll_id)
+            return {"status": "failed", "error": outcome.error or "denied"}
+        if outcome.status == "slow_down":
+            store.slow_down(poll_id, outcome.interval)
+            return _pending_response(outcome.detail)
+
+        store.schedule_next(poll_id)
+        return _pending_response(outcome.detail)
+
+    @router.post("/device/cancel")
+    def device_cancel(request: Request, poll_id: str = Form(...)):
+        require_admin(request)
+        store.pop(poll_id)
+        return {"status": "cancelled"}
+
+    return router
@@ -7,14 +7,24 @@ from typing import Dict, Any, List, Optional

 from fastapi import APIRouter, HTTPException, Query, Request, UploadFile, File, Form

-from sqlalchemy import func
+from sqlalchemy import case, func, or_
 from core.database import SessionLocal, Document, DocumentVersion
 from core.database import Session as DbSession
 from src.auth_helpers import get_current_user
+from src.constants import MAIL_ATTACHMENTS_DIR

 logger = logging.getLogger(__name__)


+def _get_session_or_404(db, session_id: str, user: Optional[str]):
+    session = db.query(DbSession).filter(DbSession.id == session_id).first()
+    if not session:
+        raise HTTPException(404, "Session not found")
+    if user and session.owner != user:
+        raise HTTPException(404, "Session not found")
+    return session
+
+
 def _aggregate_language_facets(lang_rows):
    """Sum document counts per display language for the library facet.

@@ -30,6 +40,19 @@ def _aggregate_language_facets(lang_rows):
    return out


+def _library_language_for_document(doc: Document) -> str:
+    """Return the display language used by the document library.
+
+    PDF documents are stored as markdown wrappers so the editor can preserve
+    extracted text, form fields, and annotations. The library should still
+    identify them as PDFs instead of exposing that internal wrapper format.
+    """
+    from src.pdf_form_doc import find_source_upload_id
+
+    if find_source_upload_id(doc.current_content or ""):
+        return "pdf"
+    return doc.language or "text"
+

 from routes.document_helpers import (
    DocumentCreate, DocumentUpdate, DocumentPatch,
@@ -69,17 +92,12 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
            # the doc is owner-stamped, so it lives in the library on its own.
            session = None
            if req.session_id:
-                session = db.query(DbSession).filter(DbSession.id == req.session_id).first()
-                if not session:
-                    raise HTTPException(404, "Session not found")
                # Match the lenient ownership model the rest of the app uses
                # (see _owner_filter): only block when an AUTHENTICATED user is
                # writing into a DIFFERENT user's session. In single-user /
-                # unconfigured / localhost-bypass mode the middleware leaves
-                # current_user unset (None), and those sessions are already
-                # served freely everywhere else.
-                if user and session.owner and session.owner != user:
-                    raise HTTPException(403, "Cannot create document in another user's session")
+                # unconfigured / localhost-bypass mode, falsey users preserve
+                # the existing lenient path.
+                session = _get_session_or_404(db, req.session_id, user)

            doc_id = str(uuid.uuid4())
            ver_id = str(uuid.uuid4())
@@ -171,11 +189,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
        if session_id:
            db = SessionLocal()
            try:
-                sess = db.query(DbSession).filter(DbSession.id == session_id).first()
-                if not sess:
-                    raise HTTPException(404, "Session not found")
-                if user and sess.owner and sess.owner != user:
-                    raise HTTPException(403, "Cannot import into another user's session")
+                _get_session_or_404(db, session_id, user)
            finally:
                db.close()

@@ -198,7 +212,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:

        title = os.path.splitext(meta.get("original_name") or meta.get("name") or upload_id)[0]
        try:
-            body_text = strip_pdf_content_marker(_process_pdf(pdf_path))
+            body_text = strip_pdf_content_marker(_process_pdf(pdf_path, owner=user))
        except Exception:
            body_text = None

@@ -260,18 +274,29 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
        db = SessionLocal()
        try:
            from sqlalchemy import or_
+            pdf_marker_cond = or_(
+                Document.current_content.like('%<!-- pdf_source upload_id="%'),
+                Document.current_content.like('%<!-- pdf_form_source upload_id="%'),
+            )
+            library_language_expr = case(
+                (pdf_marker_cond, "pdf"),
+                (Document.language.is_(None), "text"),
+                else_=Document.language,
+            )
            # Archived view shows ONLY archived docs; the default view excludes
            # them (NULL = legacy rows that predate the column = not archived).
            _arch_cond = (Document.archived == True) if archived else or_(
                Document.archived == False, Document.archived.is_(None))
-            # Language facet counts (owner-filtered)
+            # Language facet counts (owner-filtered). PDF documents are stored
+            # as markdown wrappers, so group by the library display language
+            # instead of the raw stored language.
            lang_q = (
-                db.query(Document.language, func.count(Document.id))
+                db.query(library_language_expr, func.count(Document.id))
                .outerjoin(DbSession, Document.session_id == DbSession.id)
                .filter(Document.is_active == True).filter(_arch_cond)
            )
            lang_q = _owner_session_filter(lang_q, user)
-            lang_rows = lang_q.group_by(Document.language).all()
+            lang_rows = lang_q.group_by(library_language_expr).all()
            languages = _aggregate_language_facets(lang_rows)

            # Session count (owner-filtered)
@@ -303,12 +328,17 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
                        Document.title.ilike(term) | Document.current_content.ilike(term)
                    )

-            # Language filter
+            # Language filter. "pdf" is a display language derived from the
+            # source marker; "markdown" excludes those wrappers.
            if language:
                if language == "text":
                    q = q.filter((Document.language == None) | (Document.language == "text"))
+                elif language == "pdf":
+                    q = q.filter(pdf_marker_cond)
                else:
                    q = q.filter(Document.language == language)
+                    if language == "markdown":
+                        q = q.filter(~pdf_marker_cond)

            # Total before pagination
            total = q.count()
@@ -332,7 +362,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
                    "session_id": doc.session_id,
                    "session_name": session_name,
                    "title": doc.title,
-                    "language": doc.language or "text",
+                    "language": _library_language_for_document(doc),
                    "preview": (doc.current_content or "")[:500],
                    "version_count": doc.version_count,
                    "created_at": (doc.created_at.isoformat() + "Z") if doc.created_at else None,
@@ -359,18 +389,17 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
        try:
            if not user:
                raise HTTPException(403, "Authentication required")
-            session = db.query(DbSession).filter(DbSession.id == session_id).first()
            # v2 review HIGH-9: raise 403 explicitly when the caller
            # can't see this session, instead of returning [] which the
            # UI treats identically to "no docs" and silently masks
            # auth failures.
-            if not session:
-                raise HTTPException(404, "Session not found")
-            if user and session.owner and session.owner != user:
-                raise HTTPException(403, "Access denied")
-            docs = db.query(Document).filter(
+            _get_session_or_404(db, session_id, user)
+            q = db.query(Document).filter(
                Document.session_id == session_id
-            ).order_by(Document.created_at.desc()).all()
+            )
+            if user:
+                q = q.filter(or_(Document.owner == user, Document.owner.is_(None)))
+            docs = q.order_by(Document.created_at.desc()).all()
            return [_doc_to_dict(d) for d in docs]
        finally:
            db.close()
@@ -437,7 +466,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
                raise HTTPException(404, "Source PDF could not be located")

            try:
-                body_text = strip_pdf_content_marker(_process_pdf(pdf_path))
+                body_text = strip_pdf_content_marker(_process_pdf(pdf_path, owner=user))
            except Exception as e:
                logger.error(f"extract_pdf_text failed for {pdf_path}: {e}")
                raise HTTPException(500, f"Extraction failed: {e}")
@@ -606,6 +635,8 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
                doc.language = req.language
            if req.session_id is not None:
                # Empty string = unlink from session
+                if req.session_id:
+                    _get_session_or_404(db, req.session_id, user)
                doc.session_id = req.session_id if req.session_id else None
                if not req.session_id:
                    # Tab closed / doc detached from its session — drop the
@@ -663,8 +694,9 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
        try:
            # Verify ownership before listing versions
            doc = db.query(Document).filter(Document.id == doc_id).first()
-            if doc:
-                _verify_doc_owner(db, doc, user)
+            if not doc:
+                raise HTTPException(404, "Document not found")
+            _verify_doc_owner(db, doc, user)
            versions = db.query(DocumentVersion).filter(
                DocumentVersion.document_id == doc_id
            ).order_by(DocumentVersion.version_number.desc()).all()
@@ -687,8 +719,9 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
        try:
            # Verify ownership
            doc = db.query(Document).filter(Document.id == doc_id).first()
-            if doc:
-                _verify_doc_owner(db, doc, user)
+            if not doc:
+                raise HTTPException(404, "Document not found")
+            _verify_doc_owner(db, doc, user)
            ver = db.query(DocumentVersion).filter(
                DocumentVersion.document_id == doc_id,
                DocumentVersion.version_number == num,
@@ -853,10 +886,10 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
        from src.llm_core import llm_call_async

        user = get_current_user(request)
-        url, model, headers = resolve_task_endpoint()
+        url, model, headers = resolve_task_endpoint(owner=user or None)
        if not url or not model:
            # Fall back to default endpoint
-            url, model, headers = resolve_endpoint("default")
+            url, model, headers = resolve_endpoint("default", owner=user or None)
        if not url or not model:
            raise HTTPException(500, "No endpoint configured for AI tidy")

@@ -1156,7 +1189,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
        settings = _load_vl_settings()
        vl_model = settings.get("vision_model", "")
        try:
-            url, model_id, headers = _resolve_vl_model(vl_model)
+            url, model_id, headers = _resolve_vl_model(vl_model, owner=user)
        except Exception as e:
            raise HTTPException(503, f"No vision model available: {e}")

@@ -1510,10 +1543,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
        # don't import from a routes file (cycle-prone). Same env override
        # as email_routes (ODYSSEUS_MAIL_ATTACHMENTS_DIR).
        from pathlib import Path as _Path
-        import os as _os
-        _DATA_DIR = _Path(__file__).resolve().parent.parent / "data"
-        _BASE = _os.environ.get("ODYSSEUS_MAIL_ATTACHMENTS_DIR", str(_DATA_DIR / "mail-attachments"))
-        _COMPOSE_DIR = _Path(_BASE) / "_compose"
+        _COMPOSE_DIR = _Path(MAIL_ATTACHMENTS_DIR) / "_compose"
        _COMPOSE_DIR.mkdir(parents=True, exist_ok=True)

        user = get_current_user(request)
@@ -1629,9 +1659,11 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
            #    context (To/Subject/In-Reply-To/References).
            try:
                from routes.email_routes import _imap, _decode_header
+                from routes.email_helpers import _q
            except Exception:
                _imap = None
                _decode_header = lambda x: x or ""
+                _q = lambda x: x or ""

            to_addr = ""
            from_name = ""
@@ -1641,7 +1673,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
            if _imap:
                try:
                    with _imap(doc.source_email_account_id or None) as conn:
-                        conn.select(doc.source_email_folder, readonly=True)
+                        conn.select(_q(doc.source_email_folder), readonly=True)
                        status, data = conn.fetch(doc.source_email_uid.encode(), "(RFC822.HEADER)")
                    if status == "OK" and data and data[0]:
                        raw_hdr = data[0][1]
@@ -71,6 +71,38 @@ def _send_smtp_message(cfg: dict, from_addr: str, recipients: list[str], message
        smtp.sendmail(from_addr, recipients, message)


+def _friendly_email_auth_error(protocol: str, host: str, error: object) -> str:
+    """Return a clearer setup error for known provider auth policies."""
+    raw = str(error or "")
+    lower = raw.lower()
+    host_lower = (host or "").lower()
+    microsoft_host = any(
+        marker in host_lower
+        for marker in (
+            "outlook.office365.com",
+            "smtp.office365.com",
+            "office365.com",
+            "outlook.com",
+            "hotmail.com",
+            "live.com",
+        )
+    )
+    microsoft_basic_auth_failure = (
+        "5.7.139" in lower
+        or "basic authentication is disabled" in lower
+        or ("authenticate failed" in lower and microsoft_host)
+        or ("authentication unsuccessful" in lower and microsoft_host)
+    )
+    if microsoft_basic_auth_failure:
+        return (
+            "Microsoft no longer accepts normal mailbox passwords for "
+            "Outlook/Office 365 IMAP/SMTP in most accounts. Odysseus "
+            "does not support Microsoft OAuth/Graph mail yet, so Outlook "
+            "accounts cannot be added with this password form."
+        )
+    return raw[:200]
+
+
 def _strip_think(text: str) -> str:
    """Email-flavored think strip — thin wrapper over the central helper.

@@ -254,16 +286,17 @@ def _cleanup_compose_uploads(tokens) -> None:
            pass


-DATA_DIR = Path(__file__).resolve().parent.parent / "data"
-SETTINGS_FILE = DATA_DIR / "settings.json"
+from src.constants import DATA_DIR as _DATA_DIR, MAIL_ATTACHMENTS_DIR, SETTINGS_FILE as _SETTINGS_FILE, SCHEDULED_EMAILS_DB
+DATA_DIR = Path(_DATA_DIR)
+SETTINGS_FILE = Path(_SETTINGS_FILE)
 # Override at deploy time via ODYSSEUS_MAIL_ATTACHMENTS_DIR. Defaults to a
 # subdir of the install's data/ tree so the app works out-of-the-box without
 # a hardcoded /home/<user>/ path.
-ATTACHMENTS_DIR = Path(os.environ.get("ODYSSEUS_MAIL_ATTACHMENTS_DIR", str(DATA_DIR / "mail-attachments")))
+ATTACHMENTS_DIR = Path(MAIL_ATTACHMENTS_DIR)
 ATTACHMENTS_DIR.mkdir(parents=True, exist_ok=True)
 COMPOSE_UPLOADS_DIR = ATTACHMENTS_DIR / "_compose"
 COMPOSE_UPLOADS_DIR.mkdir(parents=True, exist_ok=True)
-SCHEDULED_DB = DATA_DIR / "scheduled_emails.db"
+SCHEDULED_DB = Path(SCHEDULED_EMAILS_DB)


 OWNER_SCOPED_EMAIL_CACHE_TABLES = {
@@ -705,7 +738,16 @@ def _open_imap_connection(host: str, port: int, *, starttls: bool, timeout: int
    port = int(port or 993)
    if starttls:
        conn = imaplib.IMAP4(host, port, timeout=timeout)
-        conn.starttls()
+        try:
+            conn.starttls()
+        except Exception:
+            # Don't leak the open plain socket if the STARTTLS upgrade is
+            # rejected; close it before propagating. (#3174)
+            try:
+                conn.shutdown()
+            except Exception:
+                pass
+            raise
    elif port == 993:
        conn = imaplib.IMAP4_SSL(host, port, timeout=timeout)
    else:
@@ -714,6 +756,10 @@ def _open_imap_connection(host: str, port: int, *, starttls: bool, timeout: int
        conn.sock.settimeout(timeout)
    except Exception:
        pass
+    # Raise the IMAP line-length limit from the default 1 MB to 50 MB so that
+    # large mailboxes (tens of thousands of messages) don't crash with
+    # "got more than 1000000 bytes" on UID SEARCH ALL.  (#2883)
+    imaplib._MAXLINE = 50_000_000
    return conn

 def _imap_connect(account_id: str | None = None, owner: str = ""):
@@ -734,7 +780,18 @@ def _imap_connect(account_id: str | None = None, owner: str = ""):
        starttls=bool(cfg.get("imap_starttls")),
        timeout=_IMAP_TIMEOUT_SECONDS,
    )
-    conn.login(cfg["imap_user"], cfg["imap_password"])
+    try:
+        conn.login(cfg["imap_user"], cfg["imap_password"])
+    except Exception:
+        # A failed AUTHENTICATE (e.g. an Office 365 app password on an
+        # MFA-enabled tenant, #3174) otherwise orphans the already-connected
+        # socket; close it before propagating so a misconfigured account
+        # can't leak one descriptor per retry / background poller pass.
+        try:
+            conn.shutdown()
+        except Exception:
+            pass
+        raise
    return conn


@@ -798,20 +855,28 @@ def _imap(account_id: str | None = None, owner: str = ""):
 def _decode_header(raw):
    if not raw:
        return ""
-    parts = email.header.decode_header(raw)
-    decoded = []
-    for data, charset in parts:
-        if isinstance(data, bytes):
-            try:
-                decoded.append(data.decode(charset or "utf-8", errors="replace"))
-            except (LookupError, ValueError):
-                # Unknown/invalid MIME charset (e.g. a malformed or spam header
-                # like =?x-unknown-charset?B?...?=). errors="replace" only covers
-                # byte-decode errors, not codec lookup, so fall back to utf-8.
-                decoded.append(data.decode("utf-8", errors="replace"))
-        else:
-            decoded.append(data)
-    return " ".join(decoded)
+    try:
+        # make_header concatenates per RFC 2047: no spurious space between an
+        # encoded-word and adjacent plain text (plain runs keep their own
+        # whitespace), and the whitespace between two adjacent encoded-words is
+        # dropped. The old " ".join produced "Re:  Jose"-style double spaces on
+        # every non-ASCII subject or sender.
+        return str(email.header.make_header(email.header.decode_header(raw)))
+    except Exception:
+        # Malformed header or unknown/invalid MIME charset (e.g. a spam header
+        # like =?x-unknown-charset?B?...?=) makes make_header raise LookupError;
+        # fall back to a lossy per-part decode. errors="replace" only covers
+        # byte-decode errors, not codec lookup, hence the explicit utf-8 retry.
+        decoded = []
+        for data, charset in email.header.decode_header(raw):
+            if isinstance(data, bytes):
+                try:
+                    decoded.append(data.decode(charset or "utf-8", errors="replace"))
+                except (LookupError, ValueError):
+                    decoded.append(data.decode("utf-8", errors="replace"))
+            else:
+                decoded.append(data)
+        return "".join(decoded)


 def _detect_sent_folder(conn):
@@ -1136,13 +1201,9 @@ def _fetch_sender_thread_context(sender_addr: str,
    if exclude_uid:
        seen_uids.add((exclude_folder or "INBOX", str(exclude_uid)))

+    conn = None
    try:
        conn = _imap_connect(account_id, owner=owner)
-    except Exception as e:
-        logger.warning(f"sender-thread-context: imap connect failed: {e}")
-        return ""
-
-    try:
        for folder in ["INBOX", "Sent", "Archive", "Drafts"]:
            if len(blocks) >= limit:
                break
@@ -1209,11 +1270,14 @@ def _fetch_sender_thread_context(sender_addr: str,
                if atts_text:
                    lines.append(atts_text)
                blocks.append("\n".join(lines))
+    except Exception as e:
+        logger.warning(f"sender-thread-context: imap failed: {e}")
    finally:
-        try: conn.close()
-        except Exception: pass
-        try: conn.logout()
-        except Exception: pass
+        if conn:
+            try: conn.close()
+            except Exception: pass
+            try: conn.logout()
+            except Exception: pass

    if not blocks:
        return ""
@@ -1316,6 +1380,7 @@ def _pre_retrieve_context(
        if not terms_list:
            return context_snippets, terms_list

+        ctx_conn = None
        try:
            ctx_conn = _imap_connect(account_id, owner=owner)
            for folder in ["INBOX", "Sent", "Archive", "Drafts"]:
@@ -1352,12 +1417,12 @@ def _pre_retrieve_context(
                    except Exception as _e:
                        logger.warning(f"  search {folder} {term!r} failed: {_e}")
                        continue
-            try:
-                ctx_conn.logout()
-            except Exception:
-                pass
        except Exception as _e:
            logger.warning(f"IMAP context search failed: {_e}")
+        finally:
+            if ctx_conn:
+                try: ctx_conn.logout()
+                except Exception: pass

        try:
            from routes.contacts_routes import _fetch_contacts
@@ -210,7 +210,7 @@ async def _auto_summarize_pass_single(days_back: int = 1, account_id: str | None
        if auto_cal:
            for sent_name in ("Sent", "INBOX/Sent", "Sent Items", "[Gmail]/Sent Mail"):
                try:
-                    st, _ = conn.select(sent_name, readonly=True)
+                    st, _ = conn.select(_q(sent_name), readonly=True)
                    if st == "OK":
                        folders_to_scan.append(sent_name)
                        break
@@ -1046,7 +1046,7 @@ def _scheduled_poll_once() -> dict:
                try:
                    with _imap(row_account_id, owner=row_owner) as imap:
                        sent_folder = _detect_sent_folder(imap)
-                        imap.append(sent_folder, "\\Seen", None, outer.as_bytes())
+                        imap.append(_q(sent_folder), "\\Seen", None, outer.as_bytes())
                except Exception as e:
                    logger.warning(f"Failed to append scheduled {sid} to Sent: {e}")

@@ -32,9 +32,10 @@ from email.mime.multipart import MIMEMultipart

 from fastapi import APIRouter, Query, UploadFile, File, BackgroundTasks, HTTPException, Depends, Request
 from fastapi.responses import FileResponse
+from src.constants import DATA_DIR

 from src.llm_core import llm_call_async
-from src.upload_limits import read_upload_limited
+from src.upload_limits import read_upload_limited, EMAIL_COMPOSE_UPLOAD_MAX_BYTES

 from routes.email_helpers import (
    _strip_think, _extract_reply, _apply_email_style_mechanics, require_owner, require_user, _assert_owns_account,
@@ -47,6 +48,7 @@ from routes.email_helpers import (
    _extract_attachment_to_disk, _extract_html, _extract_text,
    _fetch_sender_thread_context, _pre_retrieve_context,
    _EMAIL_REPLY_SYS_PROMPT_BASE, _POOL_HOOKS,
+    _friendly_email_auth_error,
    SendEmailRequest, ExtractStyleRequest,
    ATTACHMENTS_DIR, COMPOSE_UPLOADS_DIR, SCHEDULED_DB,
    attachment_extract_dir, _email_cache_owner_clause,
@@ -56,7 +58,6 @@ from routes.email_pollers import _start_poller
 logger = logging.getLogger(__name__)

 ODYSSEUS_MAIL_ORIGIN = "odysseus-ui"
-EMAIL_COMPOSE_UPLOAD_MAX_BYTES = 25 * 1024 * 1024


 def _email_tag_owner_aliases(account_id: str | None, owner: str = "") -> list[str]:
@@ -2904,7 +2905,7 @@ def setup_email_routes():
        from pathlib import Path as _P
        import json as _json
        _slug = "".join(c if (c.isalnum() or c in "-_.@") else "_" for c in (owner or "default"))
-        path = _P(f"data/email_urgency_state_{_slug}.json")
+        path = _P(DATA_DIR) / f"email_urgency_state_{_slug}.json"
        if not path.exists():
            return {"total_unread": 0, "total_urgent": 0, "max_score": 0, "per_uid": {}}
        try:
@@ -3162,7 +3163,7 @@ def setup_email_routes():
                    try: conn.logout()
                    except Exception: pass
            except Exception as e:
-                imap_result = {"ok": False, "error": str(e)[:200]}
+                imap_result = {"ok": False, "error": _friendly_email_auth_error("IMAP", imap_host, e)}

        smtp_host = (body.get("smtp_host") or "").strip()
        if smtp_host:
@@ -3184,7 +3185,7 @@ def setup_email_routes():
                    try: smtp.quit()
                    except Exception: pass
            except Exception as e:
-                smtp_result = {"ok": False, "error": str(e)[:200]}
+                smtp_result = {"ok": False, "error": _friendly_email_auth_error("SMTP", smtp_host, e)}

        return {
            "ok": imap_result["ok"] and (smtp_result is None or smtp_result["ok"]),
@@ -7,12 +7,12 @@ import logging
 import asyncio
 from pathlib import Path
 from fastapi import APIRouter, HTTPException, Form, Depends
-from core.constants import BASE_DIR
+from core.constants import EMBEDDING_ENDPOINT_FILE, FASTEMBED_CACHE_DIR
 from core.middleware import require_admin

 logger = logging.getLogger(__name__)

-_ENDPOINT_FILE = os.path.join(BASE_DIR, "data", "embedding_endpoint.json")
+_ENDPOINT_FILE = EMBEDDING_ENDPOINT_FILE

 # Track in-progress downloads
 _downloading: dict = {}
@@ -35,13 +35,7 @@ def _cache_dir() -> str:
    default lived in /tmp, which many systems wipe on reboot — forcing a
    full re-download of the embedding model after every restart.
    """
-    env = os.environ.get("FASTEMBED_CACHE_PATH")
-    if env:
-        return env
-    return os.path.join(
-        os.path.dirname(os.path.dirname(os.path.abspath(__file__))),
-        "data", "fastembed_cache",
-    )
+    return FASTEMBED_CACHE_DIR


 def _model_cache_name(hf_source: str) -> str:
@@ -49,19 +43,35 @@ def _model_cache_name(hf_source: str) -> str:
    return "models--" + hf_source.replace("/", "--")


+def _model_cache_path(hf_source: str) -> Path:
+    """Return a confined cache path for a fastembed HF source."""
+    root = Path(_cache_dir()).expanduser().resolve()
+    raw_path = root / _model_cache_name(hf_source)
+    if raw_path.is_symlink():
+        raise ValueError("Model cache path must not be a symlink")
+    path = raw_path.resolve(strict=False)
+    try:
+        path.relative_to(root)
+    except ValueError:
+        raise ValueError("Model cache path escapes cache root")
+    return path
+
+
 def _is_downloaded(hf_source: str) -> bool:
    """Check if a model is already cached."""
-    cache = _cache_dir()
-    model_dir = os.path.join(cache, _model_cache_name(hf_source))
-    if not os.path.isdir(model_dir):
+    try:
+        model_dir = _model_cache_path(hf_source)
+    except ValueError:
+        return False
+    if not model_dir.is_dir():
        return False
    # Check for actual model files (not just empty dir)
-    snapshots = os.path.join(model_dir, "snapshots")
-    if os.path.isdir(snapshots):
-        return any(os.listdir(snapshots))
+    snapshots = model_dir / "snapshots"
+    if snapshots.is_dir():
+        return any(snapshots.iterdir())
    # Also check for blobs (older cache format)
-    blobs = os.path.join(model_dir, "blobs")
-    return os.path.isdir(blobs) and any(os.listdir(blobs))
+    blobs = model_dir / "blobs"
+    return blobs.is_dir() and any(blobs.iterdir())


 def _active_model() -> str:
@@ -119,8 +129,10 @@ def setup_embedding_routes():

            cached_size = None
            if downloaded and hf_src:
-                model_path = os.path.join(_cache_dir(), _model_cache_name(hf_src))
-                cached_size = _dir_size_mb(model_path)
+                try:
+                    cached_size = _dir_size_mb(str(_model_cache_path(hf_src)))
+                except ValueError:
+                    cached_size = None

            result.append({
                "model": m["model"],
@@ -217,8 +229,11 @@ def setup_embedding_routes():
        if not hf_src:
            raise HTTPException(400, "No cache source for this model")

-        model_path = os.path.join(_cache_dir(), _model_cache_name(hf_src))
-        if not os.path.isdir(model_path):
+        try:
+            model_path = _model_cache_path(hf_src)
+        except ValueError as e:
+            raise HTTPException(400, str(e))
+        if not model_path.is_dir():
            return {"deleted": False, "message": "Model not cached"}

        shutil.rmtree(model_path)
@@ -237,7 +252,7 @@ def setup_embedding_routes():
        }

    @router.post("/endpoint")
-    def set_endpoint(url: str = Form(...), model: str = Form("")):
+    def set_endpoint(url: str = Form(...), model: str = Form(""), api_key: str = Form("")):
        """Save a custom embedding endpoint URL."""
        url = url.strip()
        if not url:
@@ -261,6 +276,7 @@ def setup_embedding_routes():
            resp = httpx.post(
                url,
                json={"input": ["test"], "model": model or "test"},
+                headers={"Authorization": f"Bearer {api_key}"} if api_key else {},
                timeout=10,
            )
            resp.raise_for_status()
@@ -271,10 +287,16 @@ def setup_embedding_routes():
        data = {"url": url}
        if model:
            data["model"] = model
+        if api_key:
+            from src.secret_storage import encrypt
+            data["api_key"] = encrypt(api_key)
+
        _save_custom_endpoint(data)
        os.environ["EMBEDDING_URL"] = url
        if model:
            os.environ["EMBEDDING_MODEL"] = model
+        if api_key:
+            os.environ["EMBEDDING_API_KEY"] = api_key

        # Reset the RAG singleton so it picks up the new endpoint
        import src.rag_singleton as _rs
@@ -288,6 +310,16 @@ def setup_embedding_routes():
            reset_http_embed_state()
        except Exception:
            pass
+        try:
+            from src.embedding_lanes import reset_embedding_lane_state
+            reset_embedding_lane_state()
+        except Exception:
+            pass
+        try:
+            from src.tool_index import reset_tool_index
+            reset_tool_index()
+        except Exception:
+            pass

        # Reset ChromaDB client (collections will be recreated with new embeddings)
        try:
@@ -308,6 +340,7 @@ def setup_embedding_routes():
        # Remove from environment
        os.environ.pop("EMBEDDING_URL", None)
        os.environ.pop("EMBEDDING_MODEL", None)
+        os.environ.pop("EMBEDDING_API_KEY", None)

        # Reset the RAG singleton so it falls back to fastembed
        import src.rag_singleton as _rs
@@ -318,6 +351,16 @@ def setup_embedding_routes():
            reset_http_embed_state()
        except Exception:
            pass
+        try:
+            from src.embedding_lanes import reset_embedding_lane_state
+            reset_embedding_lane_state()
+        except Exception:
+            pass
+        try:
+            from src.tool_index import reset_tool_index
+            reset_tool_index()
+        except Exception:
+            pass

        # Reset ChromaDB client
        try:
@@ -16,22 +16,54 @@ from pathlib import Path

 import httpx
 from fastapi import APIRouter
-from fastapi.responses import FileResponse, Response
+from fastapi.responses import Response
+
+from src.constants import EMOJI_CACHE_DIR

 logger = logging.getLogger(__name__)

-_CACHE_DIR = Path(__file__).resolve().parent.parent / "data" / "emoji_cache"
+_CACHE_DIR = Path(EMOJI_CACHE_DIR)
 # OpenMoji "black" set = monochrome line-art SVGs. Filenames are the codepoints
 # in UPPERCASE (FE0F dropped, same as we compute), '-' joined.
 _OPENMOJI_BASE = "https://cdn.jsdelivr.net/npm/openmoji@15.0.0/black/svg"
 # codepoints like "1f600" or "1f468-200d-1f469-200d-1f467" (lowercase hex, '-' joined)
 _CODE_RE = re.compile(r"^[0-9a-f]{2,6}(?:-[0-9a-f]{2,6})*$")
-_SVG_HEADERS = {"Cache-Control": "public, max-age=31536000, immutable"}
+_MAX_SVG_BYTES = 256 * 1024
+_BLOCKED_SVG_RE = re.compile(
+    br"<\s*(?:script|foreignObject|iframe|object|embed|image)\b|"
+    br"\bon[a-z0-9_-]+\s*=",
+    re.IGNORECASE,
+)
+_EXTERNAL_REF_RE = re.compile(
+    br"\b(?:href|xlink:href)\s*=\s*['\"](?:https?:|//|data:|javascript:)",
+    re.IGNORECASE,
+)
+_SVG_SECURITY_HEADERS = {
+    "X-Content-Type-Options": "nosniff",
+    "Content-Security-Policy": "sandbox",
+    "Cross-Origin-Resource-Policy": "same-origin",
+}
+_SVG_HEADERS = {
+    "Cache-Control": "public, max-age=31536000, immutable",
+    **_SVG_SECURITY_HEADERS,
+}
 # Returned when a codepoint is unknown/unreachable: an empty (transparent) SVG,
 # so the CSS mask renders nothing instead of a solid box. Not cached, so a later
 # request can still pick up the real glyph once the CDN is reachable.
 _BLANK_SVG = b'<svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 1 1"></svg>'
-_BLANK_HEADERS = {"Cache-Control": "no-store"}
+_BLANK_HEADERS = {"Cache-Control": "no-store", **_SVG_SECURITY_HEADERS}
+
+
+def _is_safe_svg(content: bytes) -> bool:
+    if not isinstance(content, bytes) or not content:
+        return False
+    if len(content) > _MAX_SVG_BYTES:
+        return False
+    if b"<svg" not in content[:256].lower():
+        return False
+    if _BLOCKED_SVG_RE.search(content) or _EXTERNAL_REF_RE.search(content):
+        return False
+    return True


 def setup_emoji_routes() -> APIRouter:
@@ -49,14 +81,21 @@ def setup_emoji_routes() -> APIRouter:
        _CACHE_DIR.mkdir(parents=True, exist_ok=True)
        fp = _CACHE_DIR / f"{code}.svg"
        if fp.exists():
-            return FileResponse(fp, media_type="image/svg+xml", headers=_SVG_HEADERS)
+            try:
+                content = fp.read_bytes()
+                if _is_safe_svg(content):
+                    return Response(content, media_type="image/svg+xml", headers=_SVG_HEADERS)
+                fp.unlink(missing_ok=True)
+            except Exception as e:
+                logger.warning("emoji cache read %s failed: %s", code, e)
+            return _blank()

        # First time we've seen this emoji — fetch the OpenMoji black SVG + cache
        # it. OpenMoji filenames are the codepoints uppercased.
        try:
            async with httpx.AsyncClient(timeout=8.0) as client:
                r = await client.get(f"{_OPENMOJI_BASE}/{code.upper()}.svg")
-            if r.status_code == 200 and b"<svg" in r.content[:256]:
+            if r.status_code == 200 and _is_safe_svg(r.content):
                try:
                    fp.write_bytes(r.content)
                except Exception:
@@ -12,8 +12,13 @@ from fastapi import APIRouter, HTTPException, Query, Request

 from core.database import SessionLocal, GalleryImage, GalleryAlbum, ModelEndpoint
 from core.database import Session as DbSession
-from src.auth_helpers import get_current_user, require_privilege
-from src.upload_limits import read_upload_limited
+from src.auth_helpers import get_current_user, owner_filter, require_privilege
+from src.upload_limits import (
+    read_upload_limited,
+    GALLERY_UPLOAD_MAX_BYTES,
+    GALLERY_TRANSFORM_UPLOAD_MAX_BYTES,
+)
+from src.constants import GENERATED_IMAGES_DIR

 from routes.gallery_helpers import (
    GalleryPatch, _extract_exif, _image_to_dict, _owner_filter, _human_size,
@@ -21,17 +26,88 @@ from routes.gallery_helpers import (

 logger = logging.getLogger(__name__)

-GALLERY_UPLOAD_MAX_BYTES = int(os.getenv("ODYSSEUS_GALLERY_UPLOAD_MAX_BYTES", str(100 * 1024 * 1024)))
-GALLERY_TRANSFORM_UPLOAD_MAX_BYTES = int(os.getenv("ODYSSEUS_GALLERY_TRANSFORM_UPLOAD_MAX_BYTES", str(25 * 1024 * 1024)))
+
+def _current_user_is_admin(request: Request, user: str | None) -> bool:
+    if not user:
+        return False
+    auth_mgr = getattr(request.app.state, "auth_manager", None)
+    is_admin = getattr(auth_mgr, "is_admin", None)
+    if not callable(is_admin):
+        return False
+    try:
+        return bool(is_admin(user))
+    except Exception:
+        return False


 def _sanitize_gallery_filename(filename: str) -> str:
    """Return a local filename safe to join under generated_images."""
-    safe_name = re.sub(r"[^A-Za-z0-9._-]", "_", Path(filename or "").name)[:128]
+    safe_name = re.sub(r"[^A-Za-z0-9._-]", "_", Path(str(filename or "")).name)[:128]
    if not safe_name or safe_name in {".", ".."}:
        safe_name = uuid.uuid4().hex[:12]
    return safe_name

+
+GALLERY_IMAGE_DIR = Path(GENERATED_IMAGES_DIR)
+
+
+def _gallery_image_path(filename: str) -> Path:
+    """Resolve a stored gallery filename without leaving generated_images."""
+    if not isinstance(filename, str):
+        raise HTTPException(400, "Unsafe gallery filename")
+    safe_name = _sanitize_gallery_filename(filename)
+    original = str(filename or "")
+    root = GALLERY_IMAGE_DIR.resolve()
+    path = (GALLERY_IMAGE_DIR / safe_name).resolve()
+    try:
+        if os.path.commonpath([str(root), str(path)]) != str(root):
+            raise ValueError
+    except Exception:
+        raise HTTPException(400, "Unsafe gallery filename")
+    if safe_name != original:
+        raise HTTPException(400, "Unsafe gallery filename")
+    return path
+
+
+def _normalize_image_endpoint_base(url: str) -> str:
+    base = (url or "").strip().rstrip("/")
+    if base.endswith("/v1"):
+        base = base[:-3].rstrip("/")
+    return base
+
+
+def _visible_image_endpoint_query(db, owner: str | None):
+    from src.auth_helpers import owner_filter
+    q = db.query(ModelEndpoint).filter(
+        ModelEndpoint.model_type == "image",
+        ModelEndpoint.is_enabled == True,  # noqa: E712
+    )
+    return owner_filter(q, ModelEndpoint, owner)
+
+
+def _first_visible_image_endpoint(db, owner: str | None):
+    endpoints = _visible_image_endpoint_query(db, owner).all()
+    if owner:
+        for ep in endpoints:
+            if getattr(ep, "owner", None) == owner:
+                return ep
+    return endpoints[0] if endpoints else None
+
+
+def _visible_image_endpoint_for_base(db, base: str, owner: str | None):
+    target = _normalize_image_endpoint_base(base)
+    if not target:
+        return None
+    fallback = None
+    for ep in _visible_image_endpoint_query(db, owner).all():
+        if _normalize_image_endpoint_base(getattr(ep, "base_url", "")) == target:
+            if owner and getattr(ep, "owner", None) == owner:
+                return ep
+            if fallback is None:
+                fallback = ep
+    return fallback
+
+
 def setup_gallery_routes() -> APIRouter:
    router = APIRouter(tags=["gallery"])

@@ -55,6 +131,9 @@ def setup_gallery_routes() -> APIRouter:
        file_hash = hashlib.sha256(content).hexdigest()
        db = SessionLocal()
        try:
+            if album_id and user is not None:
+                _get_or_404_album(db, album_id, user)
+
            # SECURITY: scope the dup-detect to THIS user — otherwise a
            # caller can probe whether someone else uploaded the same
            # file (the response leaks the existing row's id+filename).
@@ -69,7 +148,7 @@ def setup_gallery_routes() -> APIRouter:
                return {"ok": False, "duplicate": True, "filename": existing.filename,
                        "id": existing.id, "message": "Duplicate photo skipped"}

-            img_dir = Path("data/generated_images")
+            img_dir = Path(GENERATED_IMAGES_DIR)
            img_dir.mkdir(parents=True, exist_ok=True)

            ext = file.filename.rsplit(".", 1)[-1].lower() if "." in file.filename else "png"
@@ -135,7 +214,7 @@ def setup_gallery_routes() -> APIRouter:
                raise HTTPException(400, "No image provided")

            content = await read_upload_limited(file, GALLERY_UPLOAD_MAX_BYTES, "Gallery replacement")
-            img_dir = Path("data/generated_images")
+            img_dir = Path(GENERATED_IMAGES_DIR)
            img_dir.mkdir(parents=True, exist_ok=True)
            img_path = img_dir / _sanitize_gallery_filename(img.filename)
            img_path.write_bytes(content)
@@ -211,7 +290,7 @@ def setup_gallery_routes() -> APIRouter:
            if not user or img.owner != user:
                raise HTTPException(403, "Not your image")

-            img_path = Path("data/generated_images") / img.filename
+            img_path = _gallery_image_path(img.filename)
            if not img_path.exists():
                raise HTTPException(404, "Image file not found")

@@ -248,7 +327,7 @@ def setup_gallery_routes() -> APIRouter:
        """AI upscale using img2img with the diffusion server."""
        import base64, httpx

-        require_privilege(request, "can_generate_images")
+        user = require_privilege(request, "can_generate_images")
        form = await request.form()
        file = form.get("image")
        if not file: raise HTTPException(400, "No image")
@@ -260,7 +339,7 @@ def setup_gallery_routes() -> APIRouter:
        # Find image endpoint
        db = SessionLocal()
        try:
-            ep = db.query(ModelEndpoint).filter(ModelEndpoint.model_type == "image", ModelEndpoint.is_enabled == True).first()
+            ep = _first_visible_image_endpoint(db, user)
        finally:
            db.close()

@@ -291,7 +370,7 @@ def setup_gallery_routes() -> APIRouter:
        """Style transfer using img2img with the diffusion server."""
        import base64, httpx

-        require_privilege(request, "can_generate_images")
+        user = require_privilege(request, "can_generate_images")
        form = await request.form()
        file = form.get("image")
        prompt = form.get("prompt", "")
@@ -303,7 +382,7 @@ def setup_gallery_routes() -> APIRouter:

        db = SessionLocal()
        try:
-            ep = db.query(ModelEndpoint).filter(ModelEndpoint.model_type == "image", ModelEndpoint.is_enabled == True).first()
+            ep = _first_visible_image_endpoint(db, user)
        finally:
            db.close()

@@ -505,18 +584,24 @@ def setup_gallery_routes() -> APIRouter:
            albums = q.order_by(GalleryAlbum.created_at.desc()).all()
            result = []
            for a in albums:
-                count = db.query(GalleryImage).filter(
+                _count_q = db.query(GalleryImage).filter(
                    GalleryImage.album_id == a.id, GalleryImage.is_active == True
-                ).count()
+                )
+                if user:
+                    _count_q = _count_q.filter(GalleryImage.owner == user)
+                count = _count_q.count()
                cover_url = None
                if a.cover_id:
                    cover = db.query(GalleryImage).filter(GalleryImage.id == a.cover_id).first()
                    if cover:
                        cover_url = f"/api/generated-image/{cover.filename}"
                elif count > 0:
-                    first = db.query(GalleryImage).filter(
+                    _cover_q = db.query(GalleryImage).filter(
                        GalleryImage.album_id == a.id, GalleryImage.is_active == True
-                    ).order_by(GalleryImage.created_at.desc()).first()
+                    )
+                    if user:
+                        _cover_q = _cover_q.filter(GalleryImage.owner == user)
+                    first = _cover_q.order_by(GalleryImage.created_at.desc()).first()
                    if first:
                        cover_url = f"/api/generated-image/{first.filename}"
                result.append({
@@ -649,7 +734,14 @@ def setup_gallery_routes() -> APIRouter:
            if req.favorite is not None:
                img.favorite = req.favorite
            if req.album_id is not None:
-                img.album_id = req.album_id if req.album_id else None
+                if req.album_id:
+                    # Validate the target album belongs to the caller before
+                    # moving the image into it — mirrors add_to_album, so you
+                    # cannot file your image into another user's album.
+                    _get_or_404_album(db, req.album_id, user)
+                    img.album_id = req.album_id
+                else:
+                    img.album_id = None
            db.commit()
            db.refresh(img)
            return _image_to_dict(img)
@@ -692,11 +784,11 @@ def setup_gallery_routes() -> APIRouter:
            used = set()
            with zipfile.ZipFile(buf, "w", zipfile.ZIP_DEFLATED) as zf:
                for img in imgs:
-                    src = os.path.join("data", "generated_images", img.filename)
-                    if not os.path.exists(src):
+                    src = _gallery_image_path(img.filename)
+                    if not src.exists():
                        continue
-                    ext = os.path.splitext(img.filename)[1] or ".png"
-                    base = (img.prompt or "").strip() or os.path.splitext(img.filename)[0]
+                    ext = src.suffix or ".png"
+                    base = (img.prompt or "").strip() or src.stem
                    base = re.sub(r"[^\w\-. ]+", "", base)[:60].strip() or img.id
                    name = f"{base}{ext}"
                    i = 1
@@ -818,9 +910,9 @@ def setup_gallery_routes() -> APIRouter:

            img_filename = img.filename
            # Remove the file from disk
-            img_path = os.path.join("data", "generated_images", img_filename)
-            if os.path.exists(img_path):
-                os.remove(img_path)
+            img_path = _gallery_image_path(img_filename)
+            if img_path.exists():
+                img_path.unlink()

            # Soft-delete the record
            img.is_active = False
@@ -923,7 +1015,7 @@ def setup_gallery_routes() -> APIRouter:
        the request for /v1/images/edits (multipart, inverted mask). Otherwise
        proxy through to a self-hosted diffusion server's /v1/images/inpaint."""
        import httpx
-        require_privilege(request, "can_generate_images")
+        user = require_privilege(request, "can_generate_images")
        body = await request.json()
        # Use endpoint from request body (editor dropdown) or fall back to DB lookup
        base = (body.pop("_endpoint", "") or "").rstrip("/")
@@ -942,14 +1034,11 @@ def setup_gallery_routes() -> APIRouter:
        if not base:
            db = SessionLocal()
            try:
-                eps = db.query(ModelEndpoint).filter(
-                    ModelEndpoint.is_enabled == True,
-                    ModelEndpoint.model_type == "image",
-                ).all()
-                if not eps:
+                ep = _first_visible_image_endpoint(db, user)
+                if not ep:
                    raise HTTPException(400, "No image generation endpoint configured. Serve a diffusion model via Cookbook first.")
-                base = eps[0].base_url.rstrip("/")
-                api_key = eps[0].api_key
+                base = ep.base_url.rstrip("/")
+                api_key = ep.api_key
            finally:
                db.close()
        else:
@@ -966,10 +1055,12 @@ def setup_gallery_routes() -> APIRouter:
            _target = _norm_url(base)
            db = SessionLocal()
            try:
-                for ep in db.query(ModelEndpoint).all():
-                    if _norm_url(ep.base_url) == _target:
-                        api_key = ep.api_key
-                        break
+                ep = _visible_image_endpoint_for_base(db, _target, user)
+                if ep:
+                    base = (ep.base_url or base).rstrip("/")
+                    api_key = ep.api_key
+                elif user and not _current_user_is_admin(request, user):
+                    raise HTTPException(403, "Choose a registered image endpoint")
            finally:
                db.close()

@@ -1121,7 +1212,7 @@ def setup_gallery_routes() -> APIRouter:
        you get edge blending + lighting unification while keeping the
        composition recognisable."""
        import httpx, base64 as _b64
-        require_privilege(request, "can_generate_images")
+        user = require_privilege(request, "can_generate_images")
        body = await request.json()

        image_b64 = body.get("image")
@@ -1148,23 +1239,22 @@ def setup_gallery_routes() -> APIRouter:
        if not base:
            db = SessionLocal()
            try:
-                eps = db.query(ModelEndpoint).filter(
-                    ModelEndpoint.is_enabled == True,
-                    ModelEndpoint.model_type == "image",
-                ).all()
-                if not eps:
+                ep = _first_visible_image_endpoint(db, user)
+                if not ep:
                    raise HTTPException(400, "No image generation endpoint configured.")
-                base = eps[0].base_url.rstrip("/")
-                api_key = eps[0].api_key
+                base = ep.base_url.rstrip("/")
+                api_key = ep.api_key
            finally:
                db.close()
        else:
            db = SessionLocal()
            try:
-                for ep in db.query(ModelEndpoint).all():
-                    if ep.base_url.rstrip("/").removesuffix("/v1").rstrip("/") == base.rstrip("/").removesuffix("/v1").rstrip("/"):
-                        api_key = ep.api_key
-                        break
+                ep = _visible_image_endpoint_for_base(db, base, user)
+                if ep:
+                    base = (ep.base_url or base).rstrip("/")
+                    api_key = ep.api_key
+                elif user and not _current_user_is_admin(request, user):
+                    raise HTTPException(403, "Choose a registered image endpoint")
            finally:
                db.close()

@@ -1316,6 +1406,7 @@ def setup_gallery_routes() -> APIRouter:
    @router.post("/api/image/sharpen")
    async def sharpen_image(request: Request):
        """Apply unsharp-mask sharpening to an image."""
+        require_privilege(request, "can_generate_images")
        body = await request.json()
        image_b64 = body.get("image")
        amount = body.get("amount", 50) / 100.0
@@ -1635,9 +1726,10 @@ def setup_gallery_routes() -> APIRouter:
        db = SessionLocal()
        try:
            album = _get_or_404_album(db, album_id, user)
-            db.query(GalleryImage).filter(GalleryImage.album_id == album_id).update(
-                {"album_id": None}, synchronize_session=False
-            )
+            q = db.query(GalleryImage).filter(GalleryImage.album_id == album_id)
+            if user is not None:
+                q = q.filter(GalleryImage.owner == user)
+            q.update({"album_id": None}, synchronize_session=False)
            db.delete(album)
            db.commit()
            return {"ok": True}
@@ -1708,7 +1800,7 @@ def setup_gallery_routes() -> APIRouter:
        try:
            img = _get_or_404_image(db, image_id, user)

-            img_path = Path("data/generated_images") / img.filename
+            img_path = _gallery_image_path(img.filename)
            if not img_path.exists():
                raise HTTPException(404, "Image file not found")

@@ -1726,7 +1818,7 @@ def setup_gallery_routes() -> APIRouter:
                return {"error": "Vision is disabled — enable it in Settings → Vision"}
            configured = vl_settings.get("vision_model", "")
            try:
-                chat_url, model_name, headers = _resolve_vl_model(configured)
+                chat_url, model_name, headers = _resolve_vl_model(configured, owner=user)
            except ValueError:
                return {"error": "No vision model configured — set one in Settings → Vision"}
            if not chat_url:
@@ -1807,4 +1899,3 @@ def setup_gallery_routes() -> APIRouter:
            db.close()

    return router
-
@@ -490,7 +490,13 @@ def setup_history_routes(session_manager) -> APIRouter:
            # Copy messages up to keep_count
            msgs_to_copy = source.history[:keep_count]
            for msg in msgs_to_copy:
-                new_session.add_message(ChatMessage(msg.role, msg.content, msg.metadata))
+                # Copy the metadata dict. Sharing it would let the fork's
+                # persistence (add_message -> _persist_message stamps
+                # _db_id/timestamp onto the dict) mutate the SOURCE session's
+                # in-memory messages, corrupting their _db_id and breaking
+                # edit/delete-by-id on the original conversation.
+                meta = dict(msg.metadata) if isinstance(msg.metadata, dict) else None
+                new_session.add_message(ChatMessage(msg.role, msg.content, meta))
            try:
                from src.event_bus import fire_event
                fire_event("session_created", getattr(source, 'owner', None))
@@ -522,6 +528,8 @@ def setup_history_routes(session_manager) -> APIRouter:
    async def compact_session(request: Request, session_id: str):
        """Manually trigger context compaction for a session."""
        _verify_session_owner(request, session_id)
+        from src.auth_helpers import effective_user
+        owner = effective_user(request)
        try:
            session = session_manager.get_session(session_id)
        except KeyError:
@@ -555,7 +563,7 @@ def setup_history_routes(session_manager) -> APIRouter:
            )

            # Use utility model if available
-            util_url, util_model, util_headers = resolve_endpoint("utility")
+            util_url, util_model, util_headers = resolve_endpoint("utility", owner=owner or None)
            compact_url = util_url or session.endpoint_url
            compact_model = util_model or session.model
            compact_headers = util_headers if util_url else session.headers
@@ -196,7 +196,24 @@ def setup_hwfit_routes():
        if target_context is not None:
            target_context = max(1024, min(target_context, 1000000))

-        results = rank_models(system, use_case=use_case or None, limit=limit, search=search or None, sort=sort, quant=quant or None, target_context=target_context, fit_only=fit_only)
+        rank_kwargs = {
+            "use_case": use_case or None,
+            "limit": limit,
+            "search": search or None,
+            "sort": sort,
+            "quant": quant or None,
+            "fit_only": fit_only,
+        }
+        if target_context is not None:
+            rank_kwargs["target_context"] = target_context
+        try:
+            import inspect
+            supported = set(inspect.signature(rank_models).parameters)
+            rank_kwargs = {k: v for k, v in rank_kwargs.items() if k in supported}
+        except Exception:
+            rank_kwargs.pop("target_context", None)
+            rank_kwargs.pop("fit_only", None)
+        results = rank_models(system, **rank_kwargs)
        return {"system": system, "models": results}

    @router.get("/profiles")
@@ -13,7 +13,7 @@ import httpx

 from core.database import McpServer, SessionLocal
 from core.middleware import require_admin
-from src.constants import DATA_DIR
+from src.constants import DATA_DIR, MCP_OAUTH_DIR
 from src.mcp_manager import McpManager

 logger = logging.getLogger(__name__)
@@ -23,7 +23,7 @@ router = APIRouter(prefix="/api/mcp", tags=["mcp"])

 def _mcp_oauth_base_dir() -> Path:
    """Directory that may contain OAuth files managed by Odysseus."""
-    return (Path(DATA_DIR) / "mcp_oauth").resolve(strict=False)
+    return Path(MCP_OAUTH_DIR).resolve(strict=False)


 def _resolve_mcp_oauth_path(raw_path, field_name: str) -> str:
@@ -29,11 +29,10 @@ from src.llm_core import llm_call_async
 from services.memory.memory_extractor import audit_memories
 from src.auth_helpers import get_current_user, require_user
 from src.endpoint_resolver import resolve_endpoint
-from src.upload_limits import read_upload_limited
+from src.upload_limits import read_upload_limited, MEMORY_IMPORT_MAX_BYTES

 logger = logging.getLogger(__name__)

-MEMORY_IMPORT_MAX_BYTES = int(os.getenv("ODYSSEUS_MEMORY_IMPORT_MAX_BYTES", str(10 * 1024 * 1024)))

 def setup_memory_routes(memory_manager: MemoryManager, session_manager: SessionManager, memory_vector=None):
    """Set up memory-related routes."""
@@ -371,7 +370,7 @@ def setup_memory_routes(memory_manager: MemoryManager, session_manager: SessionM
                tmp.write(content)
                tmp_path = tmp.name
            try:
-                text = _process_pdf(tmp_path)
+                text = _process_pdf(tmp_path, owner=_owner(request))
            finally:
                os.unlink(tmp_path)
        else:
@@ -4,6 +4,7 @@ import os
 import re
 import uuid
 import json
+import hashlib
 import socket
 import time as _time
 import logging
@@ -502,9 +503,71 @@ def _is_chat_model(model_id: str) -> bool:
    return True


+def _delete_orphaned_provider_auth(db, auth_id: Optional[str], exclude_ep_id: Optional[str] = None) -> bool:
+    """Delete a ProviderAuthSession once no endpoint still references it."""
+    if not auth_id:
+        return False
+    from core.database import ProviderAuthSession
+    still_referenced = db.query(ModelEndpoint.id).filter(
+        ModelEndpoint.provider_auth_id == auth_id,
+        ModelEndpoint.id != exclude_ep_id,
+    ).first()
+    if still_referenced is not None:
+        return False
+    auth_row = db.query(ProviderAuthSession).filter(ProviderAuthSession.id == auth_id).first()
+    if auth_row is None:
+        return False
+    db.delete(auth_row)
+    return True
+
+
+def _safe_detect_provider(base_url: str) -> str:
+    """Best-effort provider detection that must not break endpoint probing."""
+    try:
+        return _detect_provider(base_url)
+    except Exception as exc:
+        logger.debug("Provider detection failed for %s: %s", base_url, exc)
+        return ""
+
+
+def _safe_build_models_url(base_url: str) -> str:
+    """Build a /models URL without letting optional provider imports break probes."""
+    try:
+        return build_models_url(base_url)
+    except Exception as exc:
+        logger.debug("Model URL detection failed for %s: %s", base_url, exc)
+        return f"{(base_url or '').rstrip('/')}/models"
+
+
+def _safe_build_headers(api_key: Optional[str], base_url: str) -> dict:
+    """Build auth headers without letting optional provider imports break probes."""
+    try:
+        return build_headers(api_key, base_url)
+    except Exception as exc:
+        logger.debug("Header detection failed for %s: %s", base_url, exc)
+        return {"Authorization": f"Bearer {api_key}"} if api_key else {}
+
+
+def _is_discovery_only_provider(provider: str) -> bool:
+    return provider == "chatgpt-subscription"
+
+
+def _resolve_probe_key(ep) -> Optional[str]:
+    """API key/bearer to probe an endpoint with."""
+    try:
+        from src.endpoint_resolver import resolve_endpoint_runtime
+        _base, key = resolve_endpoint_runtime(ep, owner=getattr(ep, "owner", None))
+        return key
+    except Exception as exc:
+        logger.warning("Probe key resolution failed for %s: %s", getattr(ep, "id", "?"), exc)
+        return None
+
+
 def _probe_single_model(base: str, api_key: str, model_id: str, timeout: int = 10, with_tools: bool = False) -> dict:
    """Send a realistic completion request to a single model. Returns {status, latency_ms, error?}."""
-    provider = _detect_provider(base)
+    provider = _safe_detect_provider(base)
+    if _is_discovery_only_provider(provider):
+        return {"status": "ok", "latency_ms": 0, "skipped": True}
    messages = [
        {"role": "system", "content": "You are a helpful assistant."},
        {"role": "user", "content": "Say OK"},
@@ -523,12 +586,12 @@ def _probe_single_model(base: str, api_key: str, model_id: str, timeout: int = 1
    elif provider == "ollama":
        from src.llm_core import _build_ollama_payload
        target_url = build_chat_url(base)
-        h = build_headers(api_key, base)
+        h = _safe_build_headers(api_key, base)
        h["Content-Type"] = "application/json"
        payload = _build_ollama_payload(model_id, messages, 0.0, 5, stream=False, tools=_test_tools)
    else:
        target_url = build_chat_url(base)
-        h = build_headers(api_key, base)
+        h = _safe_build_headers(api_key, base)
        h["Content-Type"] = "application/json"
        from src.llm_core import _uses_max_completion_tokens, _restricts_temperature
        _max_key = "max_completion_tokens" if _uses_max_completion_tokens(model_id) else "max_tokens"
@@ -618,9 +681,15 @@ def _probe_endpoint(base_url: str, api_key: str = None, timeout: int = 5) -> Lis
    For Anthropic, queries their /v1/models API, falling back to hardcoded list."""
    from src.endpoint_resolver import resolve_url
    base = resolve_url(_normalize_base(base_url))
-    if _detect_provider(base) == "anthropic":
+    provider = _safe_detect_provider(base)
+    if provider == "chatgpt-subscription":
+        from src.chatgpt_subscription import fetch_available_models
+        if api_key:
+            return fetch_available_models(api_key, timeout=timeout)
+        return []
+    if provider == "anthropic":
        # Try Anthropic's /v1/models endpoint first
-        url = build_models_url(base)
+        url = _safe_build_models_url(base)
        headers = {"anthropic-version": "2023-06-01"}
        if api_key:
            headers["x-api-key"] = api_key
@@ -643,8 +712,8 @@ def _probe_endpoint(base_url: str, api_key: str = None, timeout: int = 5) -> Lis
                return []
            logger.warning(f"Anthropic /v1/models failed, using hardcoded list: {e}")
        return list(ANTHROPIC_MODELS)
-    url = build_models_url(base)
-    headers = build_headers(api_key, base)
+    url = _safe_build_models_url(base)
+    headers = _safe_build_headers(api_key, base)
    try:
        r = httpx.get(url, headers=headers, timeout=timeout, verify=llm_verify())
        r.raise_for_status()
@@ -702,7 +771,7 @@ def _ping_endpoint(base_url: str, api_key: str = None, timeout: float = 1.5) ->
    """Reachability probe that does not require installed/listed models."""
    from src.endpoint_resolver import resolve_url
    base = resolve_url(_normalize_base(base_url))
-    headers = build_headers(api_key, base)
+    headers = _safe_build_headers(api_key, base)

    # Ollama exposes /v1/models (OpenAI-compatible) AND native /api/version,
    # /api/tags. Probe native paths for Ollama-style endpoints, but avoid using
@@ -754,7 +823,22 @@ def _ping_endpoint(base_url: str, api_key: str = None, timeout: float = 1.5) ->

    try:
        r = httpx.get(base, headers=headers, timeout=timeout, verify=llm_verify())
-        return _result_from_response(r)
+        result = _result_from_response(r)
+        if result["reachable"]:
+            return result
+        sc = result.get("status_code") or 0
+        if 400 <= sc < 500 and sc not in (401, 403):
+            models_url = _safe_build_models_url(base)
+            try:
+                r2 = httpx.get(models_url, headers=headers, timeout=timeout, verify=llm_verify())
+                result2 = _result_from_response(r2)
+                if result2["reachable"]:
+                    return result2
+            except Exception:
+                pass
+        if sc:
+            return result
+        last_error = result.get("error") or last_error
    except Exception as e:
        last_error = str(e)[:120]

@@ -850,6 +934,14 @@ def _visible_models(cached_models, hidden_models, pinned_models=None):
    return [m for m in merged if m not in hidden]


+def _api_key_fingerprint(api_key: Optional[str]) -> str:
+    """Stable, non-secret label for distinguishing same-URL credentials."""
+    key = (api_key or "").strip()
+    if not key:
+        return ""
+    return hashlib.sha256(key.encode("utf-8")).hexdigest()[:8]
+
+
 def setup_model_routes(model_discovery):
    router = APIRouter(prefix="/api")

@@ -1028,7 +1120,7 @@ def setup_model_routes(model_discovery):

        for ep in endpoints:
            base = _normalize_base(ep.base_url)
-            provider = _detect_provider(base)
+            provider = _safe_detect_provider(base)
            # Merge cached + pinned models, then filter out hidden ones
            ep_model_type = getattr(ep, "model_type", None) or "llm"
            model_ids = _visible_models(
@@ -1104,8 +1196,9 @@ def setup_model_routes(model_discovery):
                raise HTTPException(401, "Not authenticated")
        except HTTPException:
            raise
-        except Exception:
-            pass
+        except Exception as e:
+            logger.error("Auth gate error in GET /api/models, failing closed: %s", e)
+            raise HTTPException(status_code=500, detail="Internal error")
        # Admins see every endpoint (they manage the global pool); regular
        # users get the owner-scoped view.
        _is_admin = False
@@ -1169,7 +1262,14 @@ def setup_model_routes(model_discovery):
            t0 = _time.time()
            try:
                import asyncio as _asyncio
-                ping = await _asyncio.to_thread(_ping_endpoint, data["base"], data.get("api_key"), 1.5)
+                # Bumped 1.5s → 3.5s. The previous 1.5s budget was clipping
+                # local vLLM endpoints on Tailscale links where the model
+                # server is still loading (Qwen3.5-122B takes 2–3 min to
+                # warm); /v1/models can take 500–2500 ms on a busy box,
+                # which pushed _ping_endpoint's full path-discovery sweep
+                # past the cap and marked the row offline despite the
+                # user actively chatting with it.
+                ping = await _asyncio.to_thread(_ping_endpoint, data["base"], data.get("api_key"), 3.5)
                lat = round((_time.time() - t0) * 1000)
                return {
                    "alive": bool(ping.get("reachable")),
@@ -1207,7 +1307,7 @@ def setup_model_routes(model_discovery):
        results = []
        for ep in endpoints:
            base = _normalize_base(ep.base_url)
-            provider = _detect_provider(base)
+            provider = _safe_detect_provider(base)
            kind = _effective_endpoint_kind(ep, base)
            cached_count = len(_cached_model_ids(ep))
            entry = {
@@ -1386,10 +1486,35 @@ def setup_model_routes(model_discovery):
                # admin-pinned IDs that a probe would never surface.
                status = "online" if (all_models or pinned) else "offline"
                ping = None
+                # When cached_models is empty, do a quick reachability probe.
+                # Bumped 1.0s → 3.5s because the user reported endpoints they
+                # were ACTIVELY chatting with showed "offline" — the previous
+                # 1s timeout was clipping live cloud endpoints (DeepSeek can
+                # take 1.5–2.5s on /v1/models when their region is under load,
+                # vLLM on a remote GPU box behind SSH can also push past 1s).
+                # 3.5s still keeps the picker render snappy in the common
+                # "everything's already cached" path because this branch only
+                # runs for endpoints with an empty cached_models.
                if not all_models and not pinned and r.is_enabled:
-                    ping = _ping_endpoint(r.base_url, r.api_key, timeout=1.0)
+                    ping = _ping_endpoint(r.base_url, r.api_key, timeout=3.5)
                    if ping.get("reachable"):
                        status = "empty"
+                        # Best-effort: if the probe came back reachable, try
+                        # to populate cached_models in the background so the
+                        # NEXT picker load shows "online" instead of "empty".
+                        # Failure here is silent — we already returned the
+                        # "empty" status, and the existing background refresh
+                        # path will eventually fill it in too.
+                        try:
+                            probed = _probe_endpoint(r.base_url, r.api_key, timeout=5)
+                            if probed:
+                                r.cached_models = json.dumps(probed)
+                                db.commit()
+                                all_models = probed
+                                visible = _visible_models(all_models, r.hidden_models, pinned)
+                                status = "online"
+                        except Exception as _refill_err:
+                            logger.debug(f"opportunistic cached_models refill failed for {r.id}: {_refill_err!r}")
                base = _normalize_base(r.base_url)
                kind = _effective_endpoint_kind(r, base)
                results.append({
@@ -1397,6 +1522,7 @@ def setup_model_routes(model_discovery):
                    "name": r.name,
                    "base_url": r.base_url,
                    "has_key": bool(r.api_key),
+                    "api_key_fingerprint": _api_key_fingerprint(r.api_key),
                    "is_enabled": r.is_enabled,
                    "models": visible,
                    "pinned_models": pinned,
@@ -1469,15 +1595,27 @@ def setup_model_routes(model_discovery):
        # re-adding manually-added endpoints under their host:port name.
        from src.auth_helpers import get_current_user as _gcu_dedup
        _caller = _gcu_dedup(request) or None
+        _incoming_api_key = api_key.strip()
        _db_dedup = SessionLocal()
        try:
-            existing = (
+            _same_url_rows = (
                _db_dedup.query(ModelEndpoint)
                .filter(ModelEndpoint.base_url == base_url)
                .filter((ModelEndpoint.owner.is_(None)) | (ModelEndpoint.owner == _caller))
                .order_by(ModelEndpoint.owner.desc())  # prefer owned over shared
-                .first()
+                .all()
            )
+            existing = None
+            _empty_key_existing = None
+            for _candidate in _same_url_rows:
+                _candidate_key = (getattr(_candidate, "api_key", None) or "").strip()
+                if _candidate_key == _incoming_api_key:
+                    existing = _candidate
+                    break
+                if _incoming_api_key and not _candidate_key and _empty_key_existing is None:
+                    _empty_key_existing = _candidate
+            if existing is None and _incoming_api_key and _empty_key_existing is not None:
+                existing = _empty_key_existing
            if existing:
                changed = False
                # Persist any incoming pinned IDs onto the existing row. An
@@ -1526,6 +1664,8 @@ def setup_model_routes(model_discovery):
                    "id": existing.id,
                    "name": existing.name,
                    "base_url": existing.base_url,
+                    "has_key": bool(existing.api_key),
+                    "api_key_fingerprint": _api_key_fingerprint(existing.api_key),
                    "models": _visible_models(
                        existing_models,
                        getattr(existing, "hidden_models", None),
@@ -1599,6 +1739,8 @@ def setup_model_routes(model_discovery):
            "id": ep_id,
            "name": name.strip(),
            "base_url": base_url,
+            "has_key": bool(api_key.strip()),
+            "api_key_fingerprint": _api_key_fingerprint(api_key),
            "models": _merge_model_ids(model_ids, _pinned),
            "pinned_models": _pinned,
            "online": bool(model_ids) or bool(_pinned) or bool(ping.get("reachable")),
@@ -2049,7 +2191,9 @@ def setup_model_routes(model_discovery):
            cleared_user_preferences = _clear_user_prefs_for_endpoint(ep_id)
            cleared_sessions = _clear_sessions_for_endpoint(db, ep.base_url)
            cleared_loaded_sessions = _clear_loaded_sessions_for_endpoint(ep.base_url)
+            auth_id = getattr(ep, "provider_auth_id", None)
            db.delete(ep)
+            cleared_provider_auth = _delete_orphaned_provider_auth(db, auth_id, exclude_ep_id=ep_id)
            db.commit()
            _invalidate_models_cache()
            _local_probe_cache["data"] = None
@@ -2059,6 +2203,7 @@ def setup_model_routes(model_discovery):
                "cleared_user_preferences": cleared_user_preferences,
                "cleared_sessions": cleared_sessions,
                "cleared_loaded_sessions": cleared_loaded_sessions,
+                "cleared_provider_auth": cleared_provider_auth,
            }
        finally:
            db.close()
@@ -11,6 +11,7 @@ from pydantic import BaseModel

 from core.database import SessionLocal, Note
 from src.auth_helpers import get_current_user
+from src.constants import DATA_DIR
 from sqlalchemy.orm.attributes import flag_modified

 logger = logging.getLogger(__name__)
@@ -95,6 +96,32 @@ def _note_to_dict(note: Note) -> Dict[str, Any]:
    }


+def _reminder_text_from_note(note: Note) -> tuple[str, str]:
+    """Return the reminder title/body from a stored note row."""
+    title = (note.title or "Note reminder").strip() or "Note reminder"
+    if note.items:
+        try:
+            items = json.loads(note.items)
+        except (json.JSONDecodeError, TypeError):
+            items = None
+        if isinstance(items, list):
+            pending: list[str] = []
+            for item in items:
+                if not isinstance(item, dict):
+                    continue
+                if item.get("done") or item.get("checked"):
+                    continue
+                text = str(item.get("text") or "").strip()
+                if text:
+                    pending.append(text)
+            if pending:
+                shown = "\n".join(f"- {text}" for text in pending[:8])
+                extra = f"\n...and {len(pending) - 8} more" if len(pending) > 8 else ""
+                return title, f"Pending ({len(pending)}):\n{shown}{extra}"
+            return title, f"{len(items)} item{'s' if len(items) != 1 else ''}"
+    return title, (note.content or "").strip()[:400]
+
+

 # ---------------------------------------------------------------------------
 # Reminder dispatch — module-level so background tasks (built-in actions)
@@ -114,8 +141,9 @@ async def dispatch_reminder(
    note_id: str,
    owner: str = "",
    queue_browser: bool = True,
+    settings_override: dict | None = None,
 ) -> dict:
-    """Fire a reminder via the configured channel (browser/email/ntfy).
+    """Fire a reminder via the configured channel (browser/email/ntfy/webhook).

    Args:
        title: short headline shown to the user
@@ -129,7 +157,7 @@ async def dispatch_reminder(
    nothing is "sent" synchronously for it — the channel just routes there.
    """
    from src.settings import load_settings
-    settings = load_settings()
+    settings = {**load_settings(), **(settings_override or {})}
    channel = settings.get("reminder_channel", "browser")
    llm_on = bool(settings.get("reminder_llm_synthesis", False))
    title = (title or "").strip()
@@ -143,7 +171,7 @@ async def dispatch_reminder(
            from datetime import datetime as _dt, timezone as _tz, timedelta as _td
            from pathlib import Path as _P
            _slug = "".join(c if (c.isalnum() or c in "-_.@") else "_" for c in (owner or "default"))
-            cache_path = _P(f"data/note_pings_{_slug}.json")
+            cache_path = _P(DATA_DIR) / f"note_pings_{_slug}.json"
            if cache_path.exists():
                cache = _json.loads(cache_path.read_text(encoding="utf-8"))
            last = cache.get(cache_key)
@@ -160,13 +188,14 @@ async def dispatch_reminder(
                # Treat those as browser-only dedupe so email reminders can be
                # retried by the backend scanner after a failed frontend path.
                should_skip = last_dt >= _dt.now(_tz.utc) - _td(minutes=25)
-                if should_skip and channel in ("email", "ntfy"):
+                if should_skip and channel in ("email", "ntfy", "webhook"):
                    should_skip = last_channel == channel
                if should_skip:
                    return {
                        "synthesis": None,
                        "email_sent": False,
                        "ntfy_sent": False,
+                        "webhook_sent": False,
                        "browser_sent": True,
                        "skipped": True,
                    }
@@ -179,9 +208,9 @@ async def dispatch_reminder(
        try:
            from src.endpoint_resolver import resolve_endpoint
            from src.llm_core import llm_call_async
-            url, model, headers = resolve_endpoint("utility")
+            url, model, headers = resolve_endpoint("utility", owner=owner or None)
            if not url:
-                url, model, headers = resolve_endpoint("default")
+                url, model, headers = resolve_endpoint("default", owner=owner or None)
            if url and model:
                raw = await llm_call_async(
                    url=url, model=model,
@@ -360,6 +389,76 @@ async def dispatch_reminder(
            email_error = str(e) or e.__class__.__name__
            logger.warning(f"Reminder email send failed: {e}")

+    webhook_sent = False
+    webhook_error = ""
+    if channel == "webhook":
+        try:
+            import httpx
+            import json as _wjson
+            from src.integrations import load_integrations
+            # Built-in payload defaults for known presets so users don't have
+            # to configure a template just to use a standard service.
+            _PRESET_TEMPLATE_DEFAULTS = {
+                "discord_webhook": '{"embeds": [{"title": "{{title}}", "description": "{{message}}", "color": 5793266}]}',
+            }
+            intg_id = settings.get("reminder_webhook_integration_id", "").strip()
+            template = settings.get("reminder_webhook_payload_template", "").strip()
+            if not intg_id:
+                webhook_error = "No webhook integration selected"
+            else:
+                intg = next(
+                    (i for i in load_integrations()
+                     if i.get("id") == intg_id and i.get("base_url")),
+                    None,
+                )
+                if not intg:
+                    webhook_error = f"Integration {intg_id!r} not found or missing base URL"
+                else:
+                    # Fall back to a built-in default for known presets so
+                    # users don't have to configure a template for standard
+                    # services like Discord.
+                    if not template:
+                        template = _PRESET_TEMPLATE_DEFAULTS.get(intg.get("preset", ""), "")
+                    if not template:
+                        webhook_error = "No payload template configured"
+                    else:
+                        # Render template: JSON-escape the values so the result
+                        # is always valid JSON regardless of special characters.
+                        # dumps() returns `"value"` — strip outer quotes.
+                        msg = (synthesis or note_body or title or "Reminder")[:4000]
+                        _t = _wjson.dumps(title or "Reminder")[1:-1]
+                        _m = _wjson.dumps(msg)[1:-1]
+                        rendered = template.replace("{{title}}", _t).replace("{{message}}", _m)
+                        hdrs = {"Content-Type": "application/json"}
+                        api_key = intg.get("api_key", "")
+                        auth_type = (intg.get("auth_type") or "none").lower()
+                        if api_key:
+                            if auth_type == "bearer":
+                                hdrs["Authorization"] = f"Bearer {api_key}"
+                            elif auth_type == "header":
+                                hdrs[intg.get("auth_header") or "Authorization"] = api_key
+                        url = intg["base_url"].rstrip("/")
+                        # SSRF guard — matches the pattern used by webhook_routes,
+                        # CalDAV, search, and embeddings. Blocks link-local / metadata
+                        # addresses (169.254.x.x) by default; set
+                        # REMINDER_WEBHOOK_BLOCK_PRIVATE_IPS=true to also block
+                        # RFC-1918 ranges for locked-down deployments.
+                        import os as _os
+                        from src.url_safety import check_outbound_url as _chk
+                        _block = _os.getenv("REMINDER_WEBHOOK_BLOCK_PRIVATE_IPS", "false").lower() == "true"
+                        _ok, _reason = _chk(url, block_private=_block)
+                        if not _ok:
+                            webhook_error = f"Webhook URL rejected: {_reason}"
+                        else:
+                            async with httpx.AsyncClient(timeout=10.0) as client:
+                                resp = await client.post(url, content=rendered.encode(), headers=hdrs)
+                                webhook_sent = resp.is_success
+                                if not webhook_sent:
+                                    webhook_error = f"Webhook returned HTTP {resp.status_code}"
+        except Exception as e:
+            webhook_error = str(e) or e.__class__.__name__
+            logger.warning(f"Reminder webhook send failed: {e}")
+
    ntfy_sent = False
    ntfy_error = ""
    if channel == "ntfy":
@@ -415,7 +514,7 @@ async def dispatch_reminder(
    # second send for the same note within 25 min. Without this, a note
    # whose due_date fires while the user has the app open got TWO emails
    # (frontend-fired here + background-fired by ping_notes 0–5 min later).
-    if (email_sent or ntfy_sent or browser_sent or local_browser_sent) and note_id:
+    if (email_sent or ntfy_sent or webhook_sent or browser_sent or local_browser_sent) and note_id:
        try:
            import json as _json
            from datetime import datetime as _dt, timezone as _tz
@@ -425,13 +524,13 @@ async def dispatch_reminder(
            _STATE = cache_path
            if _STATE is None:
                _slug = "".join(c if (c.isalnum() or c in "-_.@") else "_" for c in (owner or "default"))
-                _STATE = _P(f"data/note_pings_{_slug}.json")
+                _STATE = _P(DATA_DIR) / f"note_pings_{_slug}.json"
            _STATE.parent.mkdir(parents=True, exist_ok=True)
            try:
                _cache = cache or (_json.loads(_STATE.read_text(encoding="utf-8")) if _STATE.exists() else {})
            except Exception:
                _cache = {}
-            sent_channel = "email" if email_sent else "ntfy" if ntfy_sent else "browser"
+            sent_channel = "email" if email_sent else "ntfy" if ntfy_sent else "webhook" if webhook_sent else "browser"
            _cache[cache_key or str(note_id)] = {
                "at": _dt.now(_tz.utc).isoformat(),
                "channel": sent_channel,
@@ -441,11 +540,14 @@ async def dispatch_reminder(
            logger.debug(f"dispatch_reminder: cache write failed: {_e}")

    return {
+        "channel": channel,
        "synthesis": synthesis,
        "email_sent": email_sent,
        "email_error": email_error,
        "ntfy_sent": ntfy_sent,
        "ntfy_error": ntfy_error,
+        "webhook_sent": webhook_sent,
+        "webhook_error": webhook_error,
        "browser_sent": browser_sent or local_browser_sent,
    }

@@ -467,6 +569,23 @@ def setup_note_routes(task_scheduler=None):
    def _owner(request: Request) -> Optional[str]:
        return get_current_user(request)

+    def _is_admin_or_single_user(request: Request, user: str | None) -> bool:
+        if user == "internal-tool":
+            return True
+        if not user:
+            # require_user() already admitted this request, which only happens
+            # for auth-disabled, loopback-bypass, or unconfigured single-user
+            # modes. There is no separate non-admin account boundary there.
+            return True
+        try:
+            from core.auth import AuthManager
+            auth_mgr = getattr(request.app.state, "auth_manager", None) or AuthManager()
+            if not getattr(auth_mgr, "is_configured", True):
+                return True
+            return bool(auth_mgr.is_admin(user))
+        except Exception:
+            return False
+
    # --- LIST ---
    @router.get("")
    def list_notes(
@@ -684,20 +803,46 @@ def setup_note_routes(task_scheduler=None):
        """
        # Gate against anonymous callers — LLM synthesis can burn tokens.
        from src.auth_helpers import require_user as _ru
-        _ru(request)
+        user = _ru(request)
        body = await request.json()
-        note_id = body.get("note_id")
-        title = (body.get("title") or "").strip()
-        note_body = (body.get("body") or "").strip()
+        note_id = str(body.get("note_id") or "").strip()
        if not note_id:
            raise HTTPException(400, "note_id required")

-        # Delegate to the module-level helper so background tasks can reuse
-        # the same dispatch without an HTTP roundtrip + auth cookie.
+        caller = _owner(request)
+        is_test = note_id.startswith("test-")
+        is_admin = _is_admin_or_single_user(request, user or caller)
+        _override: dict = {}
+        if is_test:
+            if not is_admin:
+                raise HTTPException(403, "Admin only")
+            title = (body.get("title") or "Test Reminder").strip() or "Test Reminder"
+            note_body = (body.get("body") or "").strip()
+            # Optional overrides let the admin settings test button pass the
+            # current UI values directly so it never races a pending save.
+            if body.get("channel"):
+                _override["reminder_channel"] = body["channel"]
+            if body.get("webhook_integration_id"):
+                _override["reminder_webhook_integration_id"] = body["webhook_integration_id"]
+            if body.get("webhook_payload_template"):
+                _override["reminder_webhook_payload_template"] = body["webhook_payload_template"]
+        else:
+            db = SessionLocal()
+            try:
+                note = db.query(Note).filter(Note.id == note_id).first()
+                if not note:
+                    raise HTTPException(404, "Note not found")
+                if caller is not None and note.owner != caller:
+                    raise HTTPException(404, "Note not found")
+                title, note_body = _reminder_text_from_note(note)
+            finally:
+                db.close()
+
        return await dispatch_reminder(
            title=title, note_body=note_body, note_id=note_id,
-            owner=_owner(request) or "",
+            owner=caller or "",
            queue_browser=False,
+            settings_override=_override or None,
        )

    # --- REORDER NOTES ---
@@ -6,16 +6,14 @@ import uuid
 from typing import List, Tuple
 from fastapi import APIRouter, HTTPException, Query, Request, UploadFile, File, Depends
 from src.request_models import DirectoryRequest
-from core.constants import BASE_DIR, PERSONAL_DIR
+from core.constants import BASE_DIR, PERSONAL_DIR, PERSONAL_UPLOADS_DIR
 from src.rag_singleton import get_rag_manager
-from src.auth_helpers import get_current_user, require_user
+from src.auth_helpers import require_privilege, require_user
 from core.middleware import require_admin
 from src.upload_handler import secure_filename
+from src.upload_limits import PERSONAL_UPLOAD_MAX_BYTES

-UPLOADS_DIR = os.path.join(BASE_DIR, "data", "personal_uploads")
-MAX_PERSONAL_UPLOAD_BYTES = int(
-    os.getenv("ODYSSEUS_PERSONAL_UPLOAD_MAX_BYTES", str(25 * 1024 * 1024))
-)
+UPLOADS_DIR = PERSONAL_UPLOADS_DIR

 logger = logging.getLogger(__name__)

@@ -194,7 +192,7 @@ def setup_personal_routes(personal_docs_manager, rag_manager, rag_available):
    @router.post("/upload")
    async def upload_files_to_rag(request: Request, files: List[UploadFile] = File(...)):
        """Upload files directly into RAG. Supports text and PDF."""
-        user = get_current_user(request)
+        user = require_privilege(request, "can_use_documents")
        rag = _rag()
        if not rag:
            raise HTTPException(503, "RAG system is not available — is the embedding service running?")
@@ -208,8 +206,8 @@ def setup_personal_routes(personal_docs_manager, rag_manager, rag_available):
        for upload in files:
            try:
                file_path, stored_name, safe_name = _unique_personal_upload_path(upload_dir, upload.filename)
-                content_bytes = await upload.read(MAX_PERSONAL_UPLOAD_BYTES + 1)
-                if len(content_bytes) > MAX_PERSONAL_UPLOAD_BYTES:
+                content_bytes = await upload.read(PERSONAL_UPLOAD_MAX_BYTES + 1)
+                if len(content_bytes) > PERSONAL_UPLOAD_MAX_BYTES:
                    logger.warning(f"Rejected oversized personal upload: {upload.filename!r}")
                    total_failed += 1
                    continue
@@ -286,9 +284,12 @@ def setup_personal_routes(personal_docs_manager, rag_manager, rag_available):
            except ValueError:
                # commonpath raises on mixed drives / non-comparable paths
                in_uploads = False
-            if in_uploads and abs_target != base_abs and os.path.exists(abs_target):
-                os.remove(abs_target)
-                deleted_from_disk = True
+            if in_uploads and abs_target != base_abs:
+                try:
+                    os.remove(abs_target)
+                    deleted_from_disk = True
+                except FileNotFoundError:
+                    pass  # already gone — race with another request or cleanup

            # Exclude the file from the listing (persists across restarts)
            personal_docs_manager.exclude_file(filepath)
@@ -4,8 +4,9 @@ import os
 from typing import Optional
 from fastapi import APIRouter, Request
 from src.auth_helpers import get_current_user
+from src.constants import USER_PREFS_FILE

-PREFS_FILE = os.path.join("data", "user_prefs.json")
+PREFS_FILE = USER_PREFS_FILE


 def _load():
@@ -9,6 +9,7 @@ from pydantic import BaseModel, Field

 from src.request_models import PresetUpdateRequest
 from core.middleware import require_admin
+from src.auth_helpers import effective_user

 logger = logging.getLogger(__name__)

@@ -100,7 +101,8 @@ def setup_preset_routes(preset_manager) -> APIRouter:

        try:
            model_spec = data.get("model") or ""
-            url, model, headers = _resolve_model(model_spec)
+            user = effective_user(request)
+            url, model, headers = _resolve_model(model_spec, owner=user)
            result = await llm_call_async(url, model, messages, temperature=0.8, max_tokens=500, headers=headers)
            return {"success": True, "prompt": result.strip()}
        except Exception as e:
@@ -14,6 +14,7 @@ from fastapi.responses import HTMLResponse, StreamingResponse
 from pydantic import BaseModel, Field
 from src.endpoint_resolver import resolve_endpoint
 from src.auth_helpers import _auth_disabled, get_current_user
+from src.constants import DEEP_RESEARCH_DIR

 _SESSION_ID_RE = re.compile(r"^[a-zA-Z0-9-]{1,128}$")

@@ -37,13 +38,15 @@ def _first_chat_model(models) -> str:
    return (models[0] if models else "")


-def _resolve_research_endpoint(sess) -> tuple:
+def _resolve_research_endpoint(sess, owner: Optional[str] = None) -> tuple:
    """Return (endpoint_url, model, headers) for Deep Research, checking admin overrides."""
+    owner = owner or getattr(sess, "owner", None) or None
    url, model, headers = resolve_endpoint(
        "research",
        fallback_url=sess.endpoint_url,
        fallback_model=sess.model,
        fallback_headers=sess.headers,
+        owner=owner,
    )
    return url, model, headers

@@ -72,6 +75,38 @@ def _owned_enabled_endpoint(db, owner, endpoint_id=None):
    return owner_filter(q, ModelEndpoint, owner).first()


+def _resolve_endpoint_runtime(ep, owner=None, model: Optional[str] = None):
+    """Resolve a ModelEndpoint row into (chat_url, model, headers).
+
+    Mirrors endpoint_resolver.resolve_endpoint's provider-auth handling for
+    panel-selected research endpoints. ChatGPT Subscription endpoints keep
+    OAuth tokens in ProviderAuthSession, so ep.api_key is intentionally empty.
+    """
+    from src.endpoint_resolver import (
+        build_chat_url,
+        build_headers,
+        resolve_endpoint_runtime as resolve_model_endpoint_runtime,
+    )
+
+    try:
+        base, api_key = resolve_model_endpoint_runtime(ep, owner=owner)
+    except Exception as e:
+        logger.warning("Could not resolve endpoint credentials for research: %s", e)
+        return None
+
+    ep_model = (model or "").strip()
+    if not ep_model:
+        try:
+            models = json.loads(ep.cached_models) if ep.cached_models else []
+            if models:
+                ep_model = _first_chat_model(models)
+        except Exception:
+            pass
+    if not ep_model:
+        return None
+    return build_chat_url(base), ep_model, build_headers(api_key, base)
+
+
 def setup_research_routes(research_handler, session_manager=None) -> APIRouter:
    router = APIRouter(tags=["research"])

@@ -98,7 +133,7 @@ def setup_research_routes(research_handler, session_manager=None) -> APIRouter:
        if entry is not None:
            return entry.get("owner", "") == user
        # Task no longer in memory — check the persisted JSON.
-        path = Path("data/deep_research") / f"{session_id}.json"
+        path = Path(DEEP_RESEARCH_DIR) / f"{session_id}.json"
        if not path.exists():
            return False
        try:
@@ -162,7 +197,7 @@ def setup_research_routes(research_handler, session_manager=None) -> APIRouter:
    def _assert_owns_research(session_id: str, user: str) -> None:
        """404-not-403 ownership gate for a research session's on-disk JSON.
        Use BEFORE returning any data or mutating the file."""
-        path = Path("data/deep_research") / f"{session_id}.json"
+        path = Path(DEEP_RESEARCH_DIR) / f"{session_id}.json"
        if not path.exists():
            raise HTTPException(404, "Research not found")
        try:
@@ -225,7 +260,7 @@ def setup_research_routes(research_handler, session_manager=None) -> APIRouter:
    ):
        user = _require_user(request)
        """List all completed research for the Library panel."""
-        data_dir = Path("data/deep_research")
+        data_dir = Path(DEEP_RESEARCH_DIR)
        items = []
        for p in data_dir.glob("*.json"):
            try:
@@ -275,7 +310,7 @@ def setup_research_routes(research_handler, session_manager=None) -> APIRouter:
        summary, stats — used by the Library preview panel."""
        user = _require_user(request)
        _validate_session_id(session_id)
-        path = Path("data/deep_research") / f"{session_id}.json"
+        path = Path(DEEP_RESEARCH_DIR) / f"{session_id}.json"
        if not path.exists():
            raise HTTPException(404, "Research not found")
        try:
@@ -292,7 +327,7 @@ def setup_research_routes(research_handler, session_manager=None) -> APIRouter:
        """Soft-archive / restore a research report (sets `archived` in its JSON)."""
        user = _require_user(request)
        _validate_session_id(session_id)
-        path = Path("data/deep_research") / f"{session_id}.json"
+        path = Path(DEEP_RESEARCH_DIR) / f"{session_id}.json"
        if not path.exists():
            raise HTTPException(404, "Research not found")
        try:
@@ -312,7 +347,7 @@ def setup_research_routes(research_handler, session_manager=None) -> APIRouter:
        """Delete a research result from disk."""
        user = _require_user(request)
        _validate_session_id(session_id)
-        data_dir = Path("data/deep_research")
+        data_dir = Path(DEEP_RESEARCH_DIR)
        json_path = data_dir / f"{session_id}.json"
        deleted = False
        if json_path.exists():
@@ -368,7 +403,6 @@ def setup_research_routes(research_handler, session_manager=None) -> APIRouter:

        if body.endpoint_id:
            from src.database import SessionLocal
-            from src.endpoint_resolver import normalize_base, build_chat_url, build_headers
            db = SessionLocal()
            try:
                # Owner-scoped: never resolve another user's private endpoint
@@ -377,35 +411,26 @@ def setup_research_routes(research_handler, session_manager=None) -> APIRouter:
                ep = _owned_enabled_endpoint(db, user, body.endpoint_id)
                if not ep:
                    raise HTTPException(404, "Endpoint not found or disabled")
-                base = normalize_base(ep.base_url)
-                ep_url = build_chat_url(base)
-                ep_headers = build_headers(ep.api_key, base)
-                ep_model = body.model or ""
-                if not ep_model:
-                    try:
-                        import json as _json
-                        models = _json.loads(ep.cached_models) if ep.cached_models else []
-                        if models:
-                            ep_model = _first_chat_model(models)
-                    except Exception:
-                        pass
+                resolved = _resolve_endpoint_runtime(ep, owner=user, model=body.model)
+                if not resolved:
+                    raise HTTPException(400, "Endpoint is not configured with a usable model.")
+                ep_url, ep_model, ep_headers = resolved
            finally:
                db.close()
        else:
-            ep_url, ep_model, ep_headers = resolve_endpoint("research")
+            ep_url, ep_model, ep_headers = resolve_endpoint("research", owner=user)
            if not ep_url:
-                ep_url, ep_model, ep_headers = resolve_endpoint("utility")
+                ep_url, ep_model, ep_headers = resolve_endpoint("utility", owner=user)
            # When neither research nor utility is configured, use the user's
            # configured DEFAULT model (default_endpoint_id/default_model) rather
            # than arbitrarily grabbing the first enabled endpoint's first model
            # (which surfaced gpt-3.5). "Default" should mean the default model.
            if not ep_url:
-                ep_url, ep_model, ep_headers = resolve_endpoint("default")
+                ep_url, ep_model, ep_headers = resolve_endpoint("default", owner=user)
            if not ep_url:
-                ep_url, ep_model, ep_headers = resolve_endpoint("chat")
+                ep_url, ep_model, ep_headers = resolve_endpoint("chat", owner=user)
            if not ep_url:
                from src.database import SessionLocal
-                from src.endpoint_resolver import normalize_base, build_chat_url, build_headers
                db = SessionLocal()
                try:
                    # Owner-scoped first-enabled fallback: the caller's own rows
@@ -414,18 +439,9 @@ def setup_research_routes(research_handler, session_manager=None) -> APIRouter:
                    # /api/v1/chat fallback (webhook_routes._first_enabled_endpoint).
                    ep = _owned_enabled_endpoint(db, user)
                    if ep:
-                        base = normalize_base(ep.base_url)
-                        ep_url = build_chat_url(base)
-                        ep_headers = build_headers(ep.api_key, base)
-                        ep_model = ""
-                        if ep.cached_models:
-                            try:
-                                import json as _json
-                                models = _json.loads(ep.cached_models)
-                                if models:
-                                    ep_model = _first_chat_model(models)
-                            except Exception:
-                                pass
+                        resolved = _resolve_endpoint_runtime(ep, owner=user)
+                        if resolved:
+                            ep_url, ep_model, ep_headers = resolved
                finally:
                    db.close()
            if not ep_url:
@@ -494,7 +510,7 @@ def setup_research_routes(research_handler, session_manager=None) -> APIRouter:
            raise HTTPException(404, "No research found for this session")
        result = research_handler.get_result(session_id)
        if result is None:
-            p = Path("data/deep_research") / f"{session_id}.json"
+            p = Path(DEEP_RESEARCH_DIR) / f"{session_id}.json"
            if p.exists():
                d = json.loads(p.read_text(encoding="utf-8"))
                return {
@@ -534,7 +550,7 @@ def setup_research_routes(research_handler, session_manager=None) -> APIRouter:
        sources = research_handler.get_sources(session_id) or []
        query = ""

-        path = Path("data/deep_research") / f"{session_id}.json"
+        path = Path(DEEP_RESEARCH_DIR) / f"{session_id}.json"
        if path.exists():
            try:
                disk = json.loads(path.read_text(encoding="utf-8"))
@@ -572,19 +588,18 @@ def setup_research_routes(research_handler, session_manager=None) -> APIRouter:
                ep_headers = dict(r_headers)

        if not ep_url or not ep_model:
-            _merge(*resolve_endpoint("chat"))
+            _merge(*resolve_endpoint("chat", owner=user))
        if not ep_url or not ep_model:
-            _merge(*resolve_endpoint("research"))
+            _merge(*resolve_endpoint("research", owner=user))
        if not ep_url or not ep_model:
-            _merge(*resolve_endpoint("utility"))
+            _merge(*resolve_endpoint("utility", owner=user))
        if not ep_url or not ep_model:
-            # Last resort: any enabled endpoint
+            # Last resort: this user's enabled endpoint, plus legacy shared rows.
            from src.database import SessionLocal
-            from src.database import ModelEndpoint
            from src.endpoint_resolver import normalize_base, build_chat_url, build_headers
            db = SessionLocal()
            try:
-                ep = db.query(ModelEndpoint).filter(ModelEndpoint.is_enabled == True).first()
+                ep = _owned_enabled_endpoint(db, user)
                if ep:
                    base = normalize_base(ep.base_url)
                    fallback_url = build_chat_url(base)
@@ -594,7 +609,7 @@ def setup_research_routes(research_handler, session_manager=None) -> APIRouter:
                        try:
                            models = json.loads(ep.cached_models)
                            if models:
-                                fallback_model = models[0]
+                                fallback_model = _first_chat_model(models)
                        except Exception:
                            pass
                    _merge(fallback_url, fallback_model, fallback_headers)
@@ -10,8 +10,9 @@ import logging
 from core.session_manager import SessionManager
 from core.models import ChatMessage
 from src.request_models import SessionResponse
-from core.database import Session as DbSession, SessionLocal, Document, GalleryImage
-from src.auth_helpers import get_current_user, effective_user
+from core.database import Session as DbSession, SessionLocal, Document, GalleryImage, utcnow_naive
+from src.auth_helpers import get_current_user, effective_user, _auth_disabled
+from src.session_actions import is_session_recently_active


 def _sanitize_export_filename(name: str) -> str:
@@ -92,35 +93,30 @@ def _reject_compact_during_active_run(session_id: str) -> None:


 def _verify_session_owner(request: Request, session_id: str, session_manager=None):
-    """Verify the current user owns the session. Raises 404 if not.
+    """Verify the current user owns the session, honoring single-user modes.

-    Ownership is checked against the DB row when one exists (unchanged). If
-    there is no DB row but the caller owns an in-memory "ghost" session — one
-    that lives only in ``session_manager`` because it was never persisted, or
-    its DB row was removed out-of-band — fall back to the in-memory owner so the
-    user can still manage and delete it. Without this fallback such sessions are
-    listed by ``/api/sessions`` (they come from the in-memory manager) yet every
-    per-session operation 404s, making them impossible to delete (issue #1044).
-
-    ``session_manager`` is optional and defaults to ``None`` so existing callers
-    that only care about persisted sessions keep their exact prior behavior.
+    Authenticated requests must match the stored DB or in-memory owner. When
+    auth is disabled and no user is present, treat the app as single-user mode:
+    verify that the session exists, but do not compare its stored owner. This
+    keeps QA/dev instances with AUTH_ENABLED=false from rejecting owner-stamped
+    rows created while auth was previously enabled.
    """
    user = effective_user(request)
-    if not user:
-        raise HTTPException(403, "Authentication required")
+    if not user and not _auth_disabled():
+        raise HTTPException(401, "Authentication required")
    db = SessionLocal()
    try:
        row = db.query(DbSession.owner).filter(DbSession.id == session_id).first()
    finally:
        db.close()
    if row is not None:
-        if row.owner != user:
+        if user and row.owner != user:
            raise HTTPException(404, f"Session {session_id} not found")
        return
    # No DB row — allow the caller to act on an in-memory ghost they own.
    if session_manager is not None:
        ghost = getattr(session_manager, "sessions", {}).get(session_id)
-        if ghost is not None and getattr(ghost, "owner", None) == user:
+        if ghost is not None and (not user or getattr(ghost, "owner", None) == user):
            return
    raise HTTPException(404, f"Session {session_id} not found")

@@ -262,7 +258,7 @@ def setup_session_routes(session_manager: SessionManager, config: dict, webhook_
            last_msg_map = {}
            mode_map = {}
            msg_count_map = {}
-            rows = db.query(DbSession.id, DbSession.folder, DbSession.total_input_tokens, DbSession.total_output_tokens, DbSession.is_important, DbSession.created_at, DbSession.updated_at, DbSession.last_message_at, DbSession.mode, DbSession.message_count).filter(DbSession.archived == False).all()
+            rows = db.query(DbSession.id, DbSession.folder, DbSession.total_input_tokens, DbSession.total_output_tokens, DbSession.is_important, DbSession.created_at, DbSession.updated_at, DbSession.last_message_at, DbSession.mode, DbSession.message_count).filter(DbSession.archived == False, DbSession.owner == user).all()
            for row in rows:
                folder_map[row.id] = row.folder
                token_map[row.id] = (row.total_input_tokens or 0) + (row.total_output_tokens or 0)
@@ -284,12 +280,14 @@ def setup_session_routes(session_manager: SessionManager, config: dict, webhook_
                r[0] for r in db.query(Document.session_id)
                .filter(Document.is_active == True,
                        Document.current_content != None,
-                        func.trim(Document.current_content) != "")
+                        func.trim(Document.current_content) != "",
+                        Document.owner == user)
                .distinct().all()
            )
            img_session_ids = set(
                r[0] for r in db.query(GalleryImage.session_id)
-                .filter(GalleryImage.session_id != None)
+                .filter(GalleryImage.session_id != None,
+                        GalleryImage.owner == user)
                .distinct().all()
            )
        finally:
@@ -370,8 +368,13 @@ def setup_session_routes(session_manager: SessionManager, config: dict, webhook_
            pass
        elif not model_to_use:
            from src.llm_core import list_model_ids
-            ids = list_model_ids(endpoint_url, timeout=REQUEST_TIMEOUT,
-                                 headers=validation_headers)
+            ids = list_model_ids(
+                endpoint_url,
+                timeout=REQUEST_TIMEOUT,
+                headers=validation_headers,
+                owner=user,
+                endpoint_id=endpoint_id.strip() if endpoint_id else None,
+            )
            if not ids:
                raise HTTPException(400, "Cannot reach /v1/models")
            # Default to the first CHAT model — endpoints often list embedding/
@@ -385,8 +388,13 @@ def setup_session_routes(session_manager: SessionManager, config: dict, webhook_
            from src.llm_core import list_model_ids
            import os as _os
            req_base = _os.path.basename(model_to_use.rstrip("/"))
-            avail = list_model_ids(endpoint_url, timeout=REQUEST_TIMEOUT,
-                                   headers=validation_headers)
+            avail = list_model_ids(
+                endpoint_url,
+                timeout=REQUEST_TIMEOUT,
+                headers=validation_headers,
+                owner=user,
+                endpoint_id=endpoint_id.strip() if endpoint_id else None,
+            )
            if not avail:
                raise HTTPException(400, "Cannot reach /v1/models")
            if model_to_use not in avail:
@@ -543,22 +551,25 @@ def setup_session_routes(session_manager: SessionManager, config: dict, webhook_
            ids = body.get("ids", [])
        except Exception:
            ids = []
+        deleted_count = 0
        for sid in ids:
            try:
                _verify_session_owner(request, sid, session_manager)
-                session_manager.delete_session(sid)
+                
+                # Enforce "starred" protection consistent with single-session delete
                db = SessionLocal()
                try:
-                    db.query(_CM).filter(_CM.session_id == sid).delete()
-                    db.query(DbSession).filter(DbSession.id == sid).delete()
-                    db.commit()
-                except Exception:
-                    db.rollback()
+                    db_sess = db.query(DbSession).filter(DbSession.id == sid).first()
+                    if db_sess and db_sess.is_important:
+                        continue
                finally:
                    db.close()
+
+                if session_manager.delete_session(sid):
+                    deleted_count += 1
            except Exception:
                pass
-        return {"deleted": len(ids)}
+        return {"deleted": deleted_count}

    @router.delete("/session/{sid}")
    def delete_session(request: Request, sid: str):
@@ -924,7 +935,8 @@ def setup_session_routes(session_manager: SessionManager, config: dict, webhook_
        from src.endpoint_resolver import resolve_endpoint
        from src.llm_core import llm_call_async

-        url, model, headers = resolve_endpoint("utility", owner=get_current_user(request))
+        owner = getattr(session, "owner", None) or effective_user(request)
+        url, model, headers = resolve_endpoint("utility", owner=owner)
        if not url or not model:
            url, model, headers = session.endpoint_url, session.model, session.headers
        if not url or not model:
@@ -1006,7 +1018,7 @@ def setup_session_routes(session_manager: SessionManager, config: dict, webhook_
        }
        _THROWAWAY_MAX_MESSAGES = 4  # only delete if <= this many messages
        try:
-            rows = db.query(DbSession).filter(DbSession.archived == False, DbSession.owner == user).all()
+            rows = db.query(DbSession).filter(DbSession.archived == False, DbSession.owner == user).limit(2000).all()
            folder_map = {r.id: r.folder for r in rows}
            # Precompute per-session message counts in TWO aggregate queries
            # instead of 1–3 queries PER session — with many chats the per-row
@@ -1017,6 +1029,7 @@ def setup_session_routes(session_manager: SessionManager, config: dict, webhook_
                db.query(DbMsg.session_id, _sa_func.count(DbMsg.id))
                .filter(DbMsg.role == "assistant").group_by(DbMsg.session_id).all()
            )
+            cleanup_now = utcnow_naive()
            for row in rows:
                # Never delete important sessions
                if getattr(row, 'is_important', False):
@@ -1029,6 +1042,8 @@ def setup_session_routes(session_manager: SessionManager, config: dict, webhook_
                    if hasattr(session_manager, 'delete_session'):
                        session_manager.delete_session(row.id)
                    continue
+                if is_session_recently_active(row, now=cleanup_now):
+                    continue
                msg_count = _counts.get(row.id, 0)
                should_delete = False
                if msg_count == 0:
@@ -13,6 +13,7 @@ import tempfile
 from collections import namedtuple
 from pathlib import Path
 from typing import Dict, Any
+from core.platform_compat import IS_APPLE_SILICON, which_tool

 # POSIX-only: `pty`/`fcntl` transitively import `termios`, which does NOT exist
 # on Windows, so importing them unconditionally crashed app startup there
@@ -37,6 +38,7 @@ from core.platform_compat import (
    IS_WINDOWS,
    detached_popen_kwargs,
    find_bash,
+    git_bash_path,
 )


@@ -92,6 +94,7 @@ def _venv_activate_prefix(venv: str | None) -> str:
    act = venv if venv.endswith("/bin/activate") else venv.rstrip("/") + "/bin/activate"
    return f". {act} && "

+
 logger = logging.getLogger(__name__)

 PTY_SUPPORTED = pty is not None and fcntl is not None and hasattr(os, "setsid")
@@ -169,7 +172,10 @@ def _package_installed_from_probe(name: str, probe: dict) -> bool:
            and (dists.get("torch") or modules.get("torch", {}).get("real_module"))
        )
    if name == "hf_transfer":
-        return bool(dists.get("hf-transfer") or modules.get("hf_transfer", {}).get("real_module"))
+        return bool(
+            dists.get("hf-transfer")
+            or modules.get("hf_transfer", {}).get("real_module")
+        )
    return bool(dists.get(name) or modules.get(name, {}).get("real_module"))


@@ -194,8 +200,14 @@ def _package_status_note(name: str, probe: dict) -> str:
        if binaries.get("llama-server"):
            parts.append(f"native llama-server: {binaries['llama-server']}")
        if dists.get("llama-cpp-python"):
-            parts.append(f"python package: llama-cpp-python {dists['llama-cpp-python']}")
-        return "; ".join(parts) if parts else "No native llama-server or llama-cpp-python server package found."
+            parts.append(
+                f"python package: llama-cpp-python {dists['llama-cpp-python']}"
+            )
+        return (
+            "; ".join(parts)
+            if parts
+            else "No native llama-server or llama-cpp-python server package found."
+        )
    if name == "diffusers":
        if _package_installed_from_probe(name, probe):
            return f"diffusers {dists.get('diffusers', 'available')} with torch {dists.get('torch', 'available')}"
@@ -205,7 +217,9 @@ def _package_status_note(name: str, probe: dict) -> str:
    return ""


-def _package_pip_update_status(pkg: dict, probe: dict | None = None) -> PackageUpdateStatus:
+def _package_pip_update_status(
+    pkg: dict, probe: dict | None = None
+) -> PackageUpdateStatus:
    """Return whether the Dependencies UI should offer a generic pip update.

    "Installed" means Cookbook can use the dependency. It does not always mean
@@ -213,12 +227,28 @@ def _package_pip_update_status(pkg: dict, probe: dict | None = None) -> PackageU
    native llama-server can come from a package manager/source build, and a CLI
    may be on PATH without matching Python package metadata.
    """
+    if pkg.get("name") == "APFEL":
+        return PackageUpdateStatus(
+            False,
+            "",  # Note is empty because IT DOES allow for updates outside of PIP.
+        )
+
    if pkg.get("kind") == "system" or not pkg.get("pip"):
-        return PackageUpdateStatus(False, "Update this system dependency outside Odysseus.")
+        return PackageUpdateStatus(
+            False, "Update this system dependency outside Odysseus."
+        )

    name = pkg.get("name")
-    binaries = probe.get("binaries") if isinstance(probe, dict) and isinstance(probe.get("binaries"), dict) else {}
-    dists = probe.get("dists") if isinstance(probe, dict) and isinstance(probe.get("dists"), dict) else {}
+    binaries = (
+        probe.get("binaries")
+        if isinstance(probe, dict) and isinstance(probe.get("binaries"), dict)
+        else {}
+    )
+    dists = (
+        probe.get("dists")
+        if isinstance(probe, dict) and isinstance(probe.get("dists"), dict)
+        else {}
+    )

    if name == "llama_cpp" and binaries.get("llama-server"):
        return PackageUpdateStatus(
@@ -231,7 +261,9 @@ def _package_pip_update_status(pkg: dict, probe: dict | None = None) -> PackageU
            "Using a vLLM CLI on PATH without Python package metadata; update it outside Odysseus.",
        )

-    return PackageUpdateStatus(True, "Update uses pip in the selected Python environment.")
+    return PackageUpdateStatus(
+        True, "Update uses pip in the selected Python environment."
+    )


 def _prepend_user_install_bins_to_path() -> None:
@@ -250,7 +282,9 @@ def _prepend_user_install_bins_to_path() -> None:
        candidates = []
    candidates.append(os.path.expanduser("~/.local/bin"))

-    parts = os.environ.get("PATH", "").split(os.pathsep) if os.environ.get("PATH") else []
+    parts = (
+        os.environ.get("PATH", "").split(os.pathsep) if os.environ.get("PATH") else []
+    )
    changed = False
    for path in reversed([p for p in candidates if p]):
        if path not in parts:
@@ -357,9 +391,11 @@ PTY_UNSUPPORTED_ERROR = "pty_unsupported"

 class ShellExecRequest(BaseModel):
    command: str
-    timeout: int | None = None  # optional override; 0 = no timeout (run until client disconnects)
-    use_pty: bool = False       # use pseudo-TTY (for progress bars)
-    use_tmux: bool = False      # run in tmux session (survives browser disconnect)
+    timeout: int | None = (
+        None  # optional override; 0 = no timeout (run until client disconnects)
+    )
+    use_pty: bool = False  # use pseudo-TTY (for progress bars)
+    use_tmux: bool = False  # run in tmux session (survives browser disconnect)


 async def _create_shell(command: str, **kwargs):
@@ -368,8 +404,16 @@ async def _create_shell(command: str, **kwargs):
    POSIX: /bin/sh via create_subprocess_shell (unchanged behaviour).
    Windows: prefer a real bash (Git Bash/WSL) so bash-syntax commands behave
    the same as on Linux; fall back to cmd.exe when no bash is installed.
+    Powershell commands are executed directly via cmd.exe /c to avoid quoting
+    and env variable expansion errors under Git Bash.
    """
    if IS_WINDOWS:
+        # PowerShell commands (used by the frontend for Windows log-file polling
+        # and session management) must run directly — passing them through
+        # bash -c mangles $env:VAR syntax and breaks the command.
+        cmd_trim = command.strip()
+        if cmd_trim.startswith("powershell") or cmd_trim.startswith("cmd "):
+            return await asyncio.create_subprocess_shell(command, **kwargs)
        bash = find_bash()
        if bash:
            return await asyncio.create_subprocess_exec(bash, "-c", command, **kwargs)
@@ -386,9 +430,7 @@ async def _exec_shell(command: str, timeout: int = EXEC_TIMEOUT) -> Dict[str, An
            stderr=asyncio.subprocess.PIPE,
            cwd=str(Path.home()),
        )
-        stdout_b, stderr_b = await asyncio.wait_for(
-            proc.communicate(), timeout=timeout
-        )
+        stdout_b, stderr_b = await asyncio.wait_for(proc.communicate(), timeout=timeout)
        stdout = stdout_b.decode(errors="replace")[:MAX_OUTPUT]
        stderr = stderr_b.decode(errors="replace")[:MAX_OUTPUT]
        return {"stdout": stdout, "stderr": stderr, "exit_code": proc.returncode}
@@ -399,7 +441,11 @@ async def _exec_shell(command: str, timeout: int = EXEC_TIMEOUT) -> Dict[str, An
                await proc.wait()
            except ProcessLookupError:
                pass
-        return {"stdout": "", "stderr": f"Command timed out after {timeout}s", "exit_code": -1}
+        return {
+            "stdout": "",
+            "stderr": f"Command timed out after {timeout}s",
+            "exit_code": -1,
+        }
    except Exception as e:
        return {"stdout": "", "stderr": str(e), "exit_code": -1}

@@ -481,7 +527,7 @@ async def _generate_pty(cmd: str, timeout: int, request: Request):
                if idx == -1:
                    break
                line = buf[:idx].decode(errors="replace")
-                buf = buf[idx + sep_len:]
+                buf = buf[idx + sep_len :]
                if line:
                    yield f"data: {json.dumps({'stream': 'stdout', 'data': line})}\n\n"

@@ -503,7 +549,7 @@ async def _generate_pty(cmd: str, timeout: int, request: Request):
                if idx == -1:
                    break
                line = buf[:idx].decode(errors="replace")
-                buf = buf[idx + sep_len:]
+                buf = buf[idx + sep_len :]
                if line:
                    yield f"data: {json.dumps({'stream': 'stdout', 'data': line})}\n\n"
            if buf:
@@ -534,6 +580,7 @@ def _pty_read(fd: int) -> bytes | None:
    """Blocking read from PTY fd. Called via run_in_executor.
    Returns bytes on data, None on timeout (no data yet)."""
    import select
+
    r, _, _ = select.select([fd], [], [], 1.0)
    if r:
        try:
@@ -557,10 +604,10 @@ async def _generate_tmux(cmd: str, request: Request):
    script_path = TMUX_LOG_DIR / f"{session_id}.sh"
    script_path.write_text(
        f"#!/bin/bash\n"
-        f"ODYSSEUS_USER_SHELL=\"${{SHELL:-}}\"\n"
-        f"if [ -n \"$ODYSSEUS_USER_SHELL\" ] && [ -x \"$ODYSSEUS_USER_SHELL\" ]; then\n"
-        f"  ODYSSEUS_USER_PATH=\"$(\"$ODYSSEUS_USER_SHELL\" -ic 'printf \"__ODYSSEUS_PATH__%s\\n\" \"$PATH\"' 2>/dev/null | sed -n 's/^__ODYSSEUS_PATH__//p' | tail -n 1 || true)\"\n"
-        f"  if [ -n \"$ODYSSEUS_USER_PATH\" ]; then export PATH=\"$ODYSSEUS_USER_PATH:$PATH\"; fi\n"
+        f'ODYSSEUS_USER_SHELL="${{SHELL:-}}"\n'
+        f'if [ -n "$ODYSSEUS_USER_SHELL" ] && [ -x "$ODYSSEUS_USER_SHELL" ]; then\n'
+        f'  ODYSSEUS_USER_PATH="$("$ODYSSEUS_USER_SHELL" -ic \'printf "__ODYSSEUS_PATH__%s\\n" "$PATH"\' 2>/dev/null | sed -n \'s/^__ODYSSEUS_PATH__//p\' | tail -n 1 || true)"\n'
+        f'  if [ -n "$ODYSSEUS_USER_PATH" ]; then export PATH="$ODYSSEUS_USER_PATH:$PATH"; fi\n'
        f"fi\n"
        f"{cmd} 2>&1 | tee '{log_path}'\n"
        f"EC=${{PIPESTATUS[0]}}\n"
@@ -570,7 +617,9 @@ async def _generate_tmux(cmd: str, request: Request):
        encoding="utf-8",
    )
    script_path.chmod(0o755)
-    logger.info("tmux wrapper script created: session=%s path=%s", session_id, script_path)
+    logger.info(
+        "tmux wrapper script created: session=%s path=%s", session_id, script_path
+    )

    tmux_cmd = f"tmux new-session -d -s {session_id} {shlex.quote(str(script_path))}"

@@ -602,7 +651,9 @@ async def _generate_tmux(cmd: str, request: Request):
        # Read new lines from log
        try:
            if log_path.exists():
-                lines = log_path.read_text(encoding="utf-8", errors="replace").splitlines()
+                lines = log_path.read_text(
+                    encoding="utf-8", errors="replace"
+                ).splitlines()
                new_lines = lines[lines_sent:]
                for line in new_lines:
                    if line.startswith(":::EXIT_CODE:::"):
@@ -630,7 +681,9 @@ async def _generate_tmux(cmd: str, request: Request):
            # Session ended — do one final read
            await asyncio.sleep(0.5)
            if log_path.exists():
-                lines = log_path.read_text(encoding="utf-8", errors="replace").splitlines()
+                lines = log_path.read_text(
+                    encoding="utf-8", errors="replace"
+                ).splitlines()
                for line in lines[lines_sent:]:
                    if line.startswith(":::EXIT_CODE:::"):
                        try:
@@ -672,8 +725,8 @@ async def _generate_win_detached(cmd: str, request: Request):
    if bash:
        script_path = TMUX_LOG_DIR / f"{session_id}.sh"
        script_path.write_text(
-            f"{cmd} > {shlex.quote(str(log_path))} 2>&1\n"
-            f"echo $? > {shlex.quote(str(exit_path))}\n",
+            f"{cmd} > {shlex.quote(git_bash_path(log_path))} 2>&1\n"
+            f"echo $? > {shlex.quote(git_bash_path(exit_path))}\n",
            encoding="utf-8",
        )
        argv = [bash, str(script_path)]
@@ -711,7 +764,9 @@ async def _generate_win_detached(cmd: str, request: Request):
            return
        try:
            if log_path.exists():
-                lines = log_path.read_text(encoding="utf-8", errors="replace").splitlines()
+                lines = log_path.read_text(
+                    encoding="utf-8", errors="replace"
+                ).splitlines()
                for line in lines[lines_sent:]:
                    yield f"data: {json.dumps({'stream': 'stdout', 'data': line})}\n\n"
                lines_sent = len(lines)
@@ -723,11 +778,18 @@ async def _generate_win_detached(cmd: str, request: Request):
            await asyncio.sleep(0.3)
            try:
                if log_path.exists():
-                    lines = log_path.read_text(encoding="utf-8", errors="replace").splitlines()
+                    lines = log_path.read_text(
+                        encoding="utf-8", errors="replace"
+                    ).splitlines()
                    for line in lines[lines_sent:]:
                        yield f"data: {json.dumps({'stream': 'stdout', 'data': line})}\n\n"
                    lines_sent = len(lines)
-                exit_code = int((exit_path.read_text(encoding="utf-8", errors="replace").strip() or "0"))
+                exit_code = int(
+                    (
+                        exit_path.read_text(encoding="utf-8", errors="replace").strip()
+                        or "0"
+                    )
+                )
            except Exception:
                exit_code = 0
            break
@@ -753,7 +815,9 @@ def setup_shell_routes() -> APIRouter:
            return {"stdout": "", "stderr": "No command provided", "exit_code": 1}

        logger.info("User shell exec requested: length=%d", len(cmd))
-        result = await _exec_shell(cmd, timeout=EXEC_TIMEOUT)
+        result = await _exec_shell(
+            cmd, timeout=req.timeout if req.timeout is not None else EXEC_TIMEOUT
+        )
        return result

    @router.post("/api/shell/stream")
@@ -762,9 +826,11 @@ def setup_shell_routes() -> APIRouter:
        _require_admin(request)
        cmd = req.command.strip()
        if not cmd:
+
            async def empty():
                yield f"data: {json.dumps({'stream': 'stderr', 'data': 'No command provided'})}\n\n"
                yield f"data: {json.dumps({'exit_code': 1})}\n\n"
+
            return StreamingResponse(empty(), media_type="text/event-stream")

        timeout = req.timeout if req.timeout is not None else STREAM_TIMEOUT
@@ -781,7 +847,11 @@ def setup_shell_routes() -> APIRouter:
        if use_tmux:
            # tmux is POSIX-only; Windows uses a detached-process + logfile tail
            # that preserves the "survives disconnect" behaviour.
-            gen = _generate_win_detached(cmd, request) if IS_WINDOWS else _generate_tmux(cmd, request)
+            gen = (
+                _generate_win_detached(cmd, request)
+                if IS_WINDOWS
+                else _generate_tmux(cmd, request)
+            )
            return StreamingResponse(gen, media_type="text/event-stream")

        if use_pty and not IS_WINDOWS:
@@ -813,7 +883,12 @@ def setup_shell_routes() -> APIRouter:
                            chunk = await stream.read(4096)
                            if not chunk:
                                if buf:
-                                    await q.put((name, buf.decode(errors="replace").rstrip("\r\n")))
+                                    await q.put(
+                                        (
+                                            name,
+                                            buf.decode(errors="replace").rstrip("\r\n"),
+                                        )
+                                    )
                                break
                            buf += chunk
                            while True:
@@ -821,7 +896,7 @@ def setup_shell_routes() -> APIRouter:
                                if idx == -1:
                                    break
                                line = buf[:idx].decode(errors="replace")
-                                buf = buf[idx + sep_len:]
+                                buf = buf[idx + sep_len :]
                                if line:
                                    await q.put((name, line))
                    finally:
@@ -880,7 +955,12 @@ def setup_shell_routes() -> APIRouter:
        return StreamingResponse(generate(), media_type="text/event-stream")

    @router.get("/api/cookbook/packages")
-    async def list_packages(request: Request, host: str | None = None, ssh_port: str | None = None, venv: str | None = None):
+    async def list_packages(
+        request: Request,
+        host: str | None = None,
+        ssh_port: str | None = None,
+        venv: str | None = None,
+    ):
        """Check which optional packages are installed.

        Local-target packages are checked in-process. Remote-target packages
@@ -890,7 +970,13 @@ def setup_shell_routes() -> APIRouter:
        """
        _require_admin(request)
        _reject_cross_site(request)
-        import importlib, importlib.metadata as importlib_metadata, shlex, json as _json, site, sys
+        import importlib
+        import importlib.metadata as importlib_metadata
+        import shlex
+        import json as _json
+        import site
+        import sys
+
        _prepend_user_install_bins_to_path()
        importlib.invalidate_caches()
        try:
@@ -905,26 +991,115 @@ def setup_shell_routes() -> APIRouter:
                raise HTTPException(400, "Invalid ssh_port")
        packages = [
            # ── System ── OS binaries, not pip packages
-            {"name": "tmux", "pip": "", "desc": "Required for Linux/Termux Cookbook background downloads and serves", "category": "System", "target": "remote", "kind": "system", "install_hint": "Run Cookbook server setup, or install tmux with apt/pacman/dnf/apk/zypper."},
-            {"name": "docker", "pip": "", "desc": "Required only for Docker-backed launch commands", "category": "System", "target": "remote", "kind": "system", "install_hint": "Install Docker on the selected server and allow this user to run docker."},
+            {
+                "name": "tmux",
+                "pip": "",
+                "desc": "Required for Linux/Termux Cookbook background downloads and serves",
+                "category": "System",
+                "target": "remote",
+                "kind": "system",
+                "install_hint": "Run Cookbook server setup, or install tmux with apt/pacman/dnf/apk/zypper.",
+            },
+            {
+                "name": "docker",
+                "pip": "",
+                "desc": "Required only for Docker-backed launch commands",
+                "category": "System",
+                "target": "remote",
+                "kind": "system",
+                "install_hint": "Install Docker on the selected server and allow this user to run docker.",
+            },
            # ── LLM ── installs on GPU servers for model serving/downloading
-            {"name": "hf_transfer", "pip": "hf_transfer", "desc": "Fast model downloads from HuggingFace", "category": "LLM", "target": "remote"},
-            {"name": "llama_cpp", "pip": "llama-cpp-python[server]", "desc": "Serve GGUF models via llama.cpp", "category": "LLM", "target": "remote"},
-            {"name": "sglang", "pip": "sglang[all]", "desc": "Serve HF safetensors models via SGLang", "category": "LLM", "target": "remote"},
-            {"name": "vllm", "pip": "vllm", "desc": "High-throughput LLM serving engine", "category": "LLM", "target": "remote"},
+            {
+                "name": "hf_transfer",
+                "pip": "hf_transfer",
+                "desc": "Fast model downloads from HuggingFace",
+                "category": "LLM",
+                "target": "remote",
+            },
+            {
+                "name": "llama_cpp",
+                "pip": "llama-cpp-python[server]",
+                "desc": "Serve GGUF models via llama.cpp",
+                "category": "LLM",
+                "target": "remote",
+            },
+            {
+                "name": "sglang",
+                "pip": "sglang[all]",
+                "desc": "Serve HF safetensors models via SGLang",
+                "category": "LLM",
+                "target": "remote",
+            },
+            {
+                "name": "vllm",
+                "pip": "vllm",
+                "desc": "High-throughput LLM serving engine",
+                "category": "LLM",
+                "target": "remote",
+            },
+            {
+                "name": "APFEL",
+                "pip": "",
+                "desc": "OpenAI-compatible API for Apple Foundational Models on Apple Silicon",
+                "category": "LLM",
+                "target": "local",
+                "kind": "system",
+                "install_cmd": "brew install apfel",
+                "update_cmd": "brew upgrade apfel",
+                "install_hint": "Requires a native Apple Silicon Mac with Apple Foundational Models support. Installable via Homebrew on supported Macs.",
+            },
            # ── Image ── editor + diffusion model serving
-            {"name": "diffusers", "pip": "diffusers[torch]", "desc": "Image generation pipelines (SD, Flux) with PyTorch", "category": "Image", "target": "remote"},
-            {"name": "rembg", "pip": "rembg[gpu]", "desc": "AI background removal for image editor", "category": "Image", "target": "local"},
-            {"name": "realesrgan", "pip": "realesrgan", "desc": "AI denoise + upscale (Real-ESRGAN). Used by editor's Denoise and Upscale tools.", "category": "Image", "target": "local"},
+            {
+                "name": "diffusers",
+                "pip": "diffusers[torch]",
+                "desc": "Image generation pipelines (SD, Flux) with PyTorch",
+                "category": "Image",
+                "target": "remote",
+            },
+            {
+                "name": "rembg",
+                "pip": "rembg[gpu]",
+                "desc": "AI background removal for image editor",
+                "category": "Image",
+                "target": "local",
+            },
+            {
+                "name": "realesrgan",
+                "pip": "realesrgan",
+                "desc": "AI denoise + upscale (Real-ESRGAN). Used by editor's Denoise and Upscale tools.",
+                "category": "Image",
+                "target": "local",
+            },
            # ── Tools ──
-            {"name": "playwright", "pip": "playwright", "desc": "Browser automation for web tools", "category": "Tools", "target": "local"},
+            {
+                "name": "playwright",
+                "pip": "playwright",
+                "desc": "Browser automation for web tools",
+                "category": "Tools",
+                "target": "local",
+            },
        ]
+
+        # Most packages should not be installed through external means. Hence, set the default of the
+        # install_cmd and update_cmd to None, which indicates that the recommended way to install/update is through the Cookbook # server setup or pip. Only system packages, should have explicit install/update commands provided.
+        for pkg in packages:
+            pkg.setdefault("install_cmd", None)
+            pkg.setdefault("update_cmd", None)
        # Remote check: for remote-target packages, probe the selected server's
        # venv over SSH so a remote `pip install` actually reflects here.
        remote_status: dict = {}
        remote_details: dict = {}
-        remote_names = [p["name"] for p in packages if p.get("target") == "remote" and p.get("kind") != "system"]
-        remote_system_names = [p["name"] for p in packages if p.get("target") == "remote" and p.get("kind") == "system"]
+        remote_names = [
+            p["name"]
+            for p in packages
+            if p.get("target") == "remote" and p.get("kind") != "system"
+        ]
+        remote_system_names = [
+            p["name"]
+            for p in packages
+            if p.get("target") == "remote" and p.get("kind") == "system"
+        ]
        if host and remote_names:
            try:
                py = _package_probe_script(remote_names)
@@ -934,7 +1109,9 @@ def setup_shell_routes() -> APIRouter:
                inner = f"{src}python3 -c {shlex.quote(py)}"
                argv = _ssh_base_argv(host, ssh_port) + [inner]
                proc = await asyncio.create_subprocess_exec(
-                    *argv, stdout=asyncio.subprocess.PIPE, stderr=asyncio.subprocess.PIPE
+                    *argv,
+                    stdout=asyncio.subprocess.PIPE,
+                    stderr=asyncio.subprocess.PIPE,
                )
                out, _err = await asyncio.wait_for(proc.communicate(), timeout=12)
                txt = out.decode("utf-8", errors="replace").strip()
@@ -958,11 +1135,15 @@ def setup_shell_routes() -> APIRouter:
                checks = []
                for name in remote_system_names:
                    qn = shlex.quote(name)
-                    checks.append(f"if command -v {qn} >/dev/null 2>&1; then echo {qn}=1; else echo {qn}=0; fi")
+                    checks.append(
+                        f"if command -v {qn} >/dev/null 2>&1; then echo {qn}=1; else echo {qn}=0; fi"
+                    )
                inner = " ; ".join(checks)
                argv = _ssh_base_argv(host, ssh_port) + [inner]
                proc = await asyncio.create_subprocess_exec(
-                    *argv, stdout=asyncio.subprocess.PIPE, stderr=asyncio.subprocess.PIPE
+                    *argv,
+                    stdout=asyncio.subprocess.PIPE,
+                    stderr=asyncio.subprocess.PIPE,
                )
                out, _err = await asyncio.wait_for(proc.communicate(), timeout=12)
                txt = out.decode("utf-8", errors="replace").strip()
@@ -987,11 +1168,25 @@ def setup_shell_routes() -> APIRouter:
                    if note:
                        pkg["status_note"] = note
            elif pkg.get("kind") == "system":
-                pkg["installed"] = shutil.which(pkg["name"]) is not None
+                if pkg["name"] == "APFEL":
+                    pkg["applicable"] = IS_APPLE_SILICON
+                    pkg["installed"] = which_tool("apfel") is not None
+                    pkg["status_note"] = (
+                        "Available on Apple Silicon (arm64) devices; exposed through a local OpenAI-compatible API."
+                        if IS_APPLE_SILICON
+                        else "Requires a native Apple Silicon Mac with Apple Foundational Models support."
+                    )
+                else:
+                    pkg["installed"] = shutil.which(pkg["name"]) is not None
            elif pkg["name"] == "llama_cpp" and shutil.which("llama-server"):
                pkg["installed"] = True
-                pkg["status_note"] = f"native llama-server: {shutil.which('llama-server')}"
-                probe = {"binaries": {"llama-server": shutil.which("llama-server")}, "dists": {}}
+                pkg["status_note"] = (
+                    f"native llama-server: {shutil.which('llama-server')}"
+                )
+                probe = {
+                    "binaries": {"llama-server": shutil.which("llama-server")},
+                    "dists": {},
+                }
            elif pkg["name"] == "vllm":
                _vllm_cli = shutil.which("vllm")
                pkg["installed"] = _vllm_cli is not None
@@ -1014,6 +1209,12 @@ def setup_shell_routes() -> APIRouter:
                    pkg["installed"] = False
                except importlib_metadata.PackageNotFoundError:
                    pkg["installed"] = False
+                except Exception:
+                    # Installed but crashes on import — e.g. a CUDA build of
+                    # llama-cpp-python raising FileNotFoundError when the CUDA
+                    # toolkit dir is absent. One broken optional package must not
+                    # 500 the entire packages panel; report it as not usable.
+                    pkg["installed"] = False

            if pkg.get("installed"):
                update_status = _package_pip_update_status(pkg, probe)
@@ -1037,15 +1238,30 @@ def setup_shell_routes() -> APIRouter:
        """Install a package via pip. Admin only — pip install is effectively code exec."""
        _require_admin(request)
        import sys as _sys
+
        body = await request.json()
        pip_name = body.get("pip")
        if not pip_name:
            return {"ok": False, "error": "No package specified"}
        # Validate against known packages to prevent arbitrary pip install
        known = {
-            "rembg[gpu]", "hf_transfer", "llama-cpp-python[server]", "sglang[all]", "diffusers", "diffusers[torch]",
-            "TTS", "bark", "faster-whisper", "playwright", "realesrgan", "gfpgan",
-            "insightface", "onnxruntime-gpu", "onnxruntime", "hdbscan", "vllm",
+            "rembg[gpu]",
+            "hf_transfer",
+            "llama-cpp-python[server]",
+            "sglang[all]",
+            "diffusers",
+            "diffusers[torch]",
+            "TTS",
+            "bark",
+            "faster-whisper",
+            "playwright",
+            "realesrgan",
+            "gfpgan",
+            "insightface",
+            "onnxruntime-gpu",
+            "onnxruntime",
+            "hdbscan",
+            "vllm",
        }
        if pip_name not in known:
            return {"ok": False, "error": f"Unknown package: {pip_name}"}
@@ -1071,6 +1287,7 @@ def setup_shell_routes() -> APIRouter:
        """
        _require_admin(request)
        from routes.cookbook_helpers import _llama_cpp_rebuild_cmd
+
        body = await request.json()
        engine = str(body.get("engine") or "llamacpp").strip()
        if engine != "llamacpp":
@@ -1079,7 +1296,11 @@ def setup_shell_routes() -> APIRouter:
        ssh_port = body.get("ssh_port")
        cmd = _llama_cpp_rebuild_cmd()
        try:
-            argv = (_ssh_base_argv(host, ssh_port) + [cmd]) if host else ["bash", "-lc", cmd]
+            argv = (
+                (_ssh_base_argv(host, ssh_port) + [cmd])
+                if host
+                else ["bash", "-lc", cmd]
+            )
        except ValueError as e:
            raise HTTPException(400, str(e))
        try:
@@ -21,10 +21,44 @@ from src.auth_helpers import get_current_user
 logger = logging.getLogger(__name__)


-_DATA_URL_RE = re.compile(
-    r'^data:image/(?P<fmt>png|jpeg|jpg);base64,(?P<data>.+)$',
-    re.IGNORECASE | re.DOTALL,
-)
+_DATA_URL_RE = re.compile(r"^data:image/png;base64,(?P<data>.+)$", re.IGNORECASE | re.DOTALL)
+_ANY_IMAGE_DATA_URL_RE = re.compile(r"^data:image/[^;]+;base64,", re.IGNORECASE)
+_PNG_MAGIC = b"\x89PNG\r\n\x1a\n"
+_MAX_SIGNATURE_BYTES = 2 * 1024 * 1024
+_MAX_SIGNATURE_B64 = ((_MAX_SIGNATURE_BYTES + 2) // 3) * 4
+_MAX_SIGNATURE_DIMENSION = 4096
+
+
+def _normalize_signature_png(raw: str) -> str:
+    raw = (raw or "").strip()
+    m = _DATA_URL_RE.match(raw)
+    if m:
+        b64 = m.group("data")
+    elif _ANY_IMAGE_DATA_URL_RE.match(raw):
+        raise HTTPException(400, "Signature data must be a PNG image")
+    else:
+        b64 = raw
+    if len(b64) > _MAX_SIGNATURE_B64:
+        raise HTTPException(400, "Signature PNG is too large")
+    try:
+        payload = base64.b64decode(b64, validate=True)
+    except Exception:
+        raise HTTPException(400, "Signature data must be base64-encoded PNG bytes")
+    if not payload:
+        raise HTTPException(400, "Signature PNG is empty")
+    if len(payload) > _MAX_SIGNATURE_BYTES:
+        raise HTTPException(400, "Signature PNG is too large")
+    if not payload.startswith(_PNG_MAGIC):
+        raise HTTPException(400, "Signature data must be a PNG image")
+    return base64.b64encode(payload).decode("ascii")
+
+
+def _signature_dimension(value: Optional[int]) -> Optional[int]:
+    if value is None:
+        return None
+    if not isinstance(value, int) or value < 1 or value > _MAX_SIGNATURE_DIMENSION:
+        raise HTTPException(400, "Signature dimensions are invalid")
+    return value


 class SignatureCreate(BaseModel):
@@ -67,24 +101,18 @@ def setup_signature_routes() -> APIRouter:
    @router.post("/api/signatures")
    async def create_signature(request: Request, req: SignatureCreate) -> Dict[str, Any]:
        user = get_current_user(request)
-        raw = (req.data or "").strip()
-        m = _DATA_URL_RE.match(raw)
-        b64 = m.group("data") if m else raw
-        try:
-            payload = base64.b64decode(b64, validate=True)
-            if not payload:
-                raise ValueError("empty payload")
-        except Exception:
-            raise HTTPException(400, "Signature data must be base64-encoded PNG bytes")
+        b64 = _normalize_signature_png(req.data)
+        width = _signature_dimension(req.width)
+        height = _signature_dimension(req.height)

        sig = Signature(
            id=str(uuid.uuid4()),
            owner=user,
            name=(req.name or "Signature").strip() or "Signature",
            data_png=b64,
-            width=req.width,
-            height=req.height,
-            svg=req.svg,
+            width=width,
+            height=height,
+            svg=None,
        )
        db = SessionLocal()
        try:
@@ -11,6 +11,8 @@ import logging
 import re
 from typing import List, Optional

+import httpx
+
 from fastapi import APIRouter, HTTPException, Request
 from pydantic import BaseModel, Field

@@ -51,6 +53,10 @@ class SkillAddRequest(BaseModel):
    steps: List[str] = Field(default_factory=list)


+class SkillImportUrlRequest(BaseModel):
+    url: str = Field(..., min_length=8, max_length=2000)
+
+
 class SkillUpdateRequest(BaseModel):
    name: Optional[str] = None
    description: Optional[str] = None
@@ -1014,7 +1020,7 @@ def _resolve_audit_models(owner=None):
            spec = (get_setting("teacher_model", "") or "").strip()
            if spec:
                from src.ai_interaction import _resolve_model
-                t_url, t_model, t_headers = _resolve_model(spec)
+                t_url, t_model, t_headers = _resolve_model(spec, owner=owner)
                if t_url and t_model:
                    teacher = (t_url, t_model, t_headers)
    except Exception as e:
@@ -1103,6 +1109,35 @@ def setup_skills_routes(skills_manager: SkillsManager) -> APIRouter:
        idx = skills_manager.index_for(owner=user)
        return {"index": idx, "count": len(idx)}

+    @router.get("/slash-catalog")
+    async def get_slash_catalog(request: Request):
+        """Return skills that are available as slash commands.
+
+        Mirrors the agent prompt's published-skill index so the UI never offers
+        a slash command the model would not normally be allowed to discover.
+        """
+        user = _owner(request)
+        all_skills = {s.get("name"): s for s in skills_manager.load(owner=user)}
+        entries = []
+        for s in skills_manager.index_for(owner=user):
+            name = (s.get("name") or "").strip()
+            if not name:
+                continue
+            full = all_skills.get(name) or {}
+            category = (s.get("category") or full.get("category") or "general").strip() or "general"
+            entries.append({
+                "type": "skill",
+                "token": f"/{name}",
+                "name": name,
+                "category": f"Skills / {category}",
+                "help": s.get("description") or full.get("description") or "",
+                "usage": f"/{name} <request>",
+                "uses": int(full.get("uses") or 0),
+                "last_used": full.get("last_used"),
+            })
+        entries.sort(key=lambda row: row["name"])
+        return {"skills": entries, "count": len(entries)}
+
    @router.get("/builtin")
    async def list_builtin_skills(request: Request):
        """Read-only list of the agent's built-in tool capabilities (research,
@@ -1203,6 +1238,36 @@ def setup_skills_routes(skills_manager: SkillsManager) -> APIRouter:
            save_settings(settings)
        return {"ok": True, "name": name, "is_overridden": False}

+    @router.post("/import-from-url")
+    async def import_skill_from_url(request: Request, body: SkillImportUrlRequest):
+        """Install a SKILL.md bundle from a public GitHub URL (skills.sh links supported)."""
+        require_admin(request)
+        user = _owner(request)
+        from services.memory.skill_importer import (
+            SkillImportError,
+            fetch_skill_bundle,
+        )
+
+        try:
+            files, _src = fetch_skill_bundle(body.url.strip())
+            entry = skills_manager.import_bundle_from_files(
+                files,
+                owner=user,
+                source_url=body.url.strip(),
+            )
+        except SkillImportError as e:
+            raise HTTPException(400, str(e)) from e
+        except httpx.HTTPError as e:
+            logger.warning("skill import fetch failed: %s", e)
+            detail = str(e).strip() or "Could not download skill from URL"
+            raise HTTPException(502, detail) from e
+        except Exception as e:
+            logger.error("skill import failed: %s", e)
+            raise HTTPException(500, "Skill import failed") from e
+
+        _fire_skill_added(user)
+        return {"ok": True, "skill": entry, "files": len(files)}
+
    @router.post("/add")
    async def add_skill(request: Request, body: SkillAddRequest):
        user = _owner(request)
@@ -1236,6 +1301,47 @@ def setup_skills_routes(skills_manager: SkillsManager) -> APIRouter:
            _fire_skill_added(user)
        return {"ok": True, "deduped": bool(entry.get("_deduped")), "skill": entry}

+    @router.post("/{skill_id}/invoke")
+    async def invoke_skill(request: Request, skill_id: str):
+        """Build a skill-pinned prompt for slash-command invocation.
+
+        This is intentionally server-side so availability, ownership, and usage
+        accounting use the same rules as the SkillsManager.
+        """
+        user = _owner(request)
+        try:
+            body = await request.json()
+        except Exception:
+            body = {}
+        request_text = (body.get("request") or "").strip() if isinstance(body, dict) else ""
+
+        invokable = {
+            s.get("name"): s for s in skills_manager.index_for(owner=user)
+            if (s.get("name") or "").strip()
+        }
+        match = invokable.get(skill_id)
+        if not match:
+            raise HTTPException(404, "Skill is not available for slash invocation")
+
+        name = match.get("name")
+        md = skills_manager.read_skill_md(name, owner=user)
+        if md is None:
+            raise HTTPException(404, "Skill source unavailable")
+
+        skills_manager.record_use(name, owner=user)
+        message = (
+            "Apply the skill below to my request, following its Procedure / Pitfalls / Verification.\n\n"
+            f"--- BEGIN SKILL ---\n{md}\n--- END SKILL ---\n\n"
+            + (f"Request: {request_text}" if request_text else "Request: (use the skill as appropriate)")
+        )
+        return {
+            "ok": True,
+            "type": "skill",
+            "name": name,
+            "command": f"/{name}",
+            "message": message,
+        }
+
    @router.get("/{skill_id}")
    async def get_skill(request: Request, skill_id: str):
        user = _owner(request)
@@ -4,12 +4,10 @@
 from fastapi import APIRouter, HTTPException, UploadFile, File
 import logging

-from src.upload_limits import read_upload_limited
+from src.upload_limits import read_upload_limited, STT_MAX_AUDIO_BYTES

 logger = logging.getLogger(__name__)

-STT_MAX_AUDIO_BYTES = 25 * 1024 * 1024
-

 def setup_stt_routes(stt_service):
    """Setup STT routes with the provided STT service"""
@@ -11,13 +11,128 @@ from fastapi import APIRouter, HTTPException, Request
 from pydantic import BaseModel

 from core.database import SessionLocal, ScheduledTask, TaskRun
+from core.constants import internal_api_base
 from src.auth_helpers import get_current_user
+from src.constants import DATA_DIR, EMAIL_URGENCY_CACHE_DIR
 from src.task_scheduler import compute_next_run, HOUSEKEEPING_DEFAULTS
 from routes.prefs_routes import _load_for_user, _save_for_user

 logger = logging.getLogger(__name__)


+def _maybe_cascade_calendar_event(task) -> None:
+    """Delete the linked calendar event when a cookbook_serve task is
+    removed. Two lookup strategies:
+
+      1. PRIMARY — `cookbook_event_uid` marker stashed in task.prompt
+         by cookbookSchedule.js right after creating the event. Direct
+         UID match, no ambiguity.
+
+      2. FALLBACK — for tasks created before the marker was wired up
+         (or when the PATCH to add the marker failed silently), scan
+         the Cookbook calendar for events whose summary equals the
+         task name and delete the matches.
+
+    Best-effort throughout: errors are logged but never block the task
+    deletion itself."""
+    if not task or task.task_type != "action" or task.action != "cookbook_serve":
+        return
+
+    import httpx
+    from core.middleware import INTERNAL_TOOL_HEADER, INTERNAL_TOOL_TOKEN
+    headers = {INTERNAL_TOOL_HEADER: INTERNAL_TOOL_TOKEN}
+    if task.owner:
+        headers["X-Odysseus-Owner"] = task.owner
+
+    # Strategy 1: explicit UID marker in prompt.
+    event_uid = ""
+    if task.prompt:
+        try:
+            cfg = json.loads(task.prompt)
+            if isinstance(cfg, dict):
+                event_uid = (cfg.get("cookbook_event_uid") or "").strip()
+        except Exception:
+            pass
+
+    def _try_delete(uid: str) -> bool:
+        try:
+            with httpx.Client(timeout=10) as client:
+                r = client.delete(
+                    f"{internal_api_base()}/api/calendar/events/{uid}",
+                    headers=headers,
+                )
+                if r.status_code >= 400:
+                    logger.info(
+                        f"task delete: cascade calendar event {uid} returned "
+                        f"HTTP {r.status_code}"
+                    )
+                    return False
+                return True
+        except Exception as e:
+            logger.warning(f"task delete: cascade calendar event {uid} failed: {e}")
+            return False
+
+    if event_uid:
+        _try_delete(event_uid)
+        return
+
+    # Strategy 2: scan the Cookbook calendar for matching summaries.
+    # Only runs for tasks missing the marker (old tasks or PATCH failures).
+    if not task.name:
+        return
+    try:
+        with httpx.Client(timeout=10) as client:
+            # Find the Cookbook calendar.
+            cal_r = client.get(f"{internal_api_base()}/api/calendar/calendars", headers=headers)
+            if cal_r.status_code >= 400:
+                return
+            cals = (cal_r.json() or {}).get("calendars", [])
+            cookbook_cal = next(
+                (c for c in cals if (c.get("name") or "").lower() == "cookbook"),
+                None,
+            )
+            if not cookbook_cal:
+                return
+            cal_href = cookbook_cal.get("href") or cookbook_cal.get("id") or ""
+            # List events in a wide window to catch recurring + upcoming.
+            from datetime import datetime as _dt, timedelta as _td, timezone as _tz
+            now = _dt.now(_tz.utc)
+            start = (now - _td(days=30)).isoformat()
+            end = (now + _td(days=365)).isoformat()
+            ev_r = client.get(
+                f"{internal_api_base()}/api/calendar/events",
+                params={"start": start, "end": end, "calendar": cal_href},
+                headers=headers,
+            )
+            if ev_r.status_code >= 400:
+                return
+            events = (ev_r.json() or {}).get("events", [])
+            # Match by exact summary. Tasks named "Serve: <model>" are
+            # created from the schedule modal; the event's summary mirrors
+            # the task name 1:1 by design.
+            target = (task.name or "").strip()
+            uids_to_delete = set()
+            for ev in events:
+                if (ev.get("summary") or "").strip() != target:
+                    continue
+                uid = ev.get("uid") or ev.get("id") or ""
+                # Strip the "::occurrence" suffix on recurring expansions —
+                # we want to delete the MASTER once, not each instance.
+                if "::" in uid:
+                    uid = uid.split("::", 1)[0]
+                if uid:
+                    uids_to_delete.add(uid)
+            for uid in uids_to_delete:
+                _try_delete(uid)
+            if uids_to_delete:
+                logger.info(
+                    f"task delete: cascade matched {len(uids_to_delete)} calendar event(s) "
+                    f"by summary fallback for task {task.id} ({target!r})"
+                )
+    except Exception as e:
+        logger.warning(f"task delete: cascade fallback scan failed: {e}")
+
+
 class TaskCreate(BaseModel):
    name: Optional[str] = None
    prompt: Optional[str] = None
@@ -178,20 +293,24 @@ def setup_task_routes(task_scheduler) -> APIRouter:
    def _owner(request: Request):
        return get_current_user(request)

-    async def _generate_task_name(prompt: str) -> str:
+    async def _generate_task_name(prompt: str, owner: Optional[str] = None) -> str:
        """Use LLM to generate a short task name from the prompt."""
        try:
            from src.llm_core import llm_call_async
            from core.database import Session as DbSession
            db = SessionLocal()
            try:
-                recent = db.query(DbSession).filter(
+                q = db.query(DbSession).filter(
                    DbSession.endpoint_url.isnot(None),
                    DbSession.model.isnot(None),
-                ).order_by(DbSession.created_at.desc()).first()
+                )
+                if owner:
+                    q = q.filter(DbSession.owner == owner)
+                recent = q.order_by(DbSession.created_at.desc()).first()
                if not recent:
                    return prompt[:50].strip()
                url, model = recent.endpoint_url, recent.model
+                headers = recent.headers or {}
            finally:
                db.close()

@@ -202,6 +321,7 @@ def setup_task_routes(task_scheduler) -> APIRouter:
                    {"role": "user", "content": prompt[:500]},
                ],
                max_tokens=20,
+                headers=headers,
                timeout=15,
            )
            title = result.strip().strip('"\'').strip()
@@ -316,6 +436,20 @@ def setup_task_routes(task_scheduler) -> APIRouter:
        except Exception:
            return False

+    def _validate_then_task_id(db, then_task_id: Optional[str], user: Optional[str], current_task_id: Optional[str] = None) -> Optional[str]:
+        target_id = (then_task_id or "").strip()
+        if not target_id:
+            return None
+        if current_task_id and target_id == current_task_id:
+            raise HTTPException(400, "Task cannot chain to itself")
+        q = db.query(ScheduledTask).filter(ScheduledTask.id == target_id)
+        if user:
+            q = q.filter(ScheduledTask.owner == user)
+        target = q.first()
+        if not target:
+            raise HTTPException(404, "Chained task not found")
+        return target.id
+
    @router.post("")
    async def create_task(request: Request, req: TaskCreate):
        user = _owner(request)
@@ -352,7 +486,7 @@ def setup_task_routes(task_scheduler) -> APIRouter:
                from src.builtin_actions import BUILTIN_ACTION_INFO
                name = BUILTIN_ACTION_INFO.get(req.action, req.action or "Action Task")
            elif req.prompt:
-                name = await _generate_task_name(req.prompt)
+                name = await _generate_task_name(req.prompt, owner=user)
            else:
                name = "Untitled Task"

@@ -379,11 +513,21 @@ def setup_task_routes(task_scheduler) -> APIRouter:
        task_id = str(uuid.uuid4())
        db = SessionLocal()
        try:
+            then_task_id = _validate_then_task_id(db, req.then_task_id, user)
            notifications_enabled = (
                False if req.task_type == "action" and req.notifications_enabled is None
                else bool(req.notifications_enabled) if req.notifications_enabled is not None
                else True
            )
+            # Validate chained task belongs to same owner
+            if req.then_task_id:
+                chain_target = db.query(ScheduledTask).filter(
+                    ScheduledTask.id == req.then_task_id
+                ).first()
+                if not chain_target:
+                    raise HTTPException(400, "Chained task not found")
+                if chain_target.owner != user:
+                    raise HTTPException(403, "Cannot chain to another user's task")
            task = ScheduledTask(
                id=task_id,
                owner=user,
@@ -405,7 +549,7 @@ def setup_task_routes(task_scheduler) -> APIRouter:
                output_target=req.output_target,
                model=req.model or None,
                endpoint_url=req.endpoint_url or None,
-                then_task_id=req.then_task_id or None,
+                then_task_id=then_task_id,
                webhook_token=webhook_token,
                notifications_enabled=notifications_enabled,
            )
@@ -487,7 +631,7 @@ def setup_task_routes(task_scheduler) -> APIRouter:

        removed_files = 0
        if action == "check_email_urgency":
-            cache_dir = Path("data/email_urgency_cache")
+            cache_dir = Path(EMAIL_URGENCY_CACHE_DIR)
            if cache_dir.exists():
                for child in cache_dir.glob("*.json"):
                    try:
@@ -496,7 +640,7 @@ def setup_task_routes(task_scheduler) -> APIRouter:
                    except Exception:
                        pass
            owner_slug = "".join(c if (c.isalnum() or c in "-_.@") else "_" for c in (user or "default"))
-            for state_path in [Path(f"data/email_urgency_state_{owner_slug}.json")]:
+            for state_path in [Path(DATA_DIR) / f"email_urgency_state_{owner_slug}.json"]:
                try:
                    if state_path.exists():
                        state_path.unlink()
@@ -558,7 +702,7 @@ def setup_task_routes(task_scheduler) -> APIRouter:
            if req.trigger_count is not None:
                task.trigger_count = req.trigger_count
            if req.then_task_id is not None:
-                task.then_task_id = req.then_task_id or None
+                task.then_task_id = _validate_then_task_id(db, req.then_task_id, user, current_task_id=task.id)
            if req.notifications_enabled is not None:
                task.notifications_enabled = bool(req.notifications_enabled)
            if req.cron_expression is not None:
@@ -616,6 +760,12 @@ def setup_task_routes(task_scheduler) -> APIRouter:
                raise HTTPException(404, "Task not found")
            if user and task.owner != user:
                raise HTTPException(403, "Access denied")
+            # Cascade: cookbook_serve tasks may have a linked calendar
+            # event (created via the "Create event in calendar" toggle
+            # in the schedule modal). If so, delete the calendar event
+            # too so the calendar doesn't end up holding a phantom event
+            # for a task that no longer exists.
+            _maybe_cascade_calendar_event(task)
            db.delete(task)
            db.commit()
            return {"ok": True}
@@ -833,7 +983,7 @@ def setup_task_routes(task_scheduler) -> APIRouter:
            "tag", "label", "move", "archive", "delete", "mark", "schedule",
        )
        try:
-            from src.agent_tools import get_mcp_manager
+            from src.tool_utils import get_mcp_manager
            mcp = get_mcp_manager()
            if mcp:
                for tool in mcp.get_all_tools():
@@ -928,6 +1078,7 @@ def setup_task_routes(task_scheduler) -> APIRouter:
        desc = (body.get("description") or "").strip()
        if not desc:
            return {"success": False, "message": "Nothing to parse"}
+        user = _owner(request)

        now = _dt.now()
        # Give the model the current date/time + weekday so relative phrasing
@@ -954,9 +1105,9 @@ def setup_task_routes(task_scheduler) -> APIRouter:
            "use cron '0 H * * 1-5'. Keep the prompt actionable and self-contained."
        )
        try:
-            url, model, headers = resolve_endpoint("utility")
+            url, model, headers = resolve_endpoint("utility", owner=user or None)
            if not url:
-                url, model, headers = resolve_endpoint("default")
+                url, model, headers = resolve_endpoint("default", owner=user or None)
            if not (url and model):
                return {"success": False, "message": "No model endpoint configured"}
            raw = await llm_call_async(
@@ -13,9 +13,43 @@ from src.upload_handler import count_recent_uploads
 logger = logging.getLogger(__name__)

 router = APIRouter(prefix="/api/upload", tags=["upload"])
+UPLOAD_RESPONSE_HEADERS = {"X-Content-Type-Options": "nosniff"}

 def setup_upload_routes(upload_handler):
    """Setup upload routes with the provided handler"""
+
+    def _upload_root() -> str:
+        from src.constants import UPLOAD_DIR
+        return os.path.realpath(getattr(upload_handler, "upload_dir", UPLOAD_DIR))
+
+    def _path_inside_upload_dir(path: str) -> bool:
+        try:
+            return os.path.commonpath([_upload_root(), os.path.realpath(path)]) == _upload_root()
+        except Exception:
+            return False
+
+    def _resolve_upload_path(file_id: str) -> str:
+        from src.constants import UPLOAD_DIR
+        upload_root = getattr(upload_handler, "upload_dir", UPLOAD_DIR)
+        direct = os.path.join(upload_root, file_id)
+        if os.path.lexists(direct):
+            if not _path_inside_upload_dir(direct):
+                raise HTTPException(403, "Access denied")
+            if os.path.isfile(direct):
+                return direct
+            raise HTTPException(404, "File not found")
+
+        for root, _dirs, files in os.walk(upload_root, followlinks=False):
+            if file_id not in files:
+                continue
+            path = os.path.join(root, file_id)
+            if not _path_inside_upload_dir(path):
+                raise HTTPException(403, "Access denied")
+            if os.path.isfile(path):
+                return path
+            raise HTTPException(404, "File not found")
+
+        raise HTTPException(404, "File not found")
    
    @router.post("")
    async def api_upload(request: Request, files: List[UploadFile] = File(...)):
@@ -91,23 +125,11 @@ def setup_upload_routes(upload_handler):
        client isn't downloading the full-resolution photo just to show it tiny."""
        if not upload_handler.validate_upload_id(file_id):
            raise HTTPException(400, "Invalid file ID")
-        # Search upload directories for the file
-        from src.constants import UPLOAD_DIR
        import mimetypes as _mt
-        path = os.path.join(UPLOAD_DIR, file_id)
-        if not os.path.exists(path):
-            for root, dirs, files in os.walk(UPLOAD_DIR):
-                if file_id in files:
-                    path = os.path.join(root, file_id)
-                    break
-            else:
-                raise HTTPException(404, "File not found")
-        if not upload_handler.inside_base_dir(path):
-            raise HTTPException(403, "Access denied")
        # Look up original filename and owner from uploads.json
        original_name = file_id
        info = None
-        uploads_db = os.path.join(UPLOAD_DIR, "uploads.json")
+        uploads_db = os.path.join(_upload_root(), "uploads.json")
        if os.path.exists(uploads_db):
            with open(uploads_db, encoding="utf-8") as f:
                db = json.load(f)
@@ -123,13 +145,14 @@ def setup_upload_routes(upload_handler):
                raise HTTPException(403, "Access denied")
            if file_owner != current_user and not auth_mgr.is_admin(current_user):
                raise HTTPException(404, "File not found")
-        mime = _mt.guess_type(path)[0] or "application/octet-stream"
+        path = _resolve_upload_path(file_id)
+        mime = (info or {}).get("mime") or _mt.guess_type(path)[0] or "application/octet-stream"
        from fastapi.responses import FileResponse
        # Downscaled thumbnail for image previews — generated once and cached.
        if thumb and mime.startswith("image/"):
            try:
                from PIL import Image, ImageOps
-                thumb_dir = os.path.join(UPLOAD_DIR, ".thumbs")
+                thumb_dir = os.path.join(_upload_root(), ".thumbs")
                os.makedirs(thumb_dir, exist_ok=True)
                thumb_path = os.path.join(thumb_dir, file_id + ".jpg")
                if (not os.path.exists(thumb_path)
@@ -145,17 +168,21 @@ def setup_upload_routes(upload_handler):
                    if im.mode not in ("RGB", "L"):
                        im = im.convert("RGB")
                    im.save(thumb_path, "JPEG", quality=80)
-                return FileResponse(thumb_path, media_type="image/jpeg")
+                return FileResponse(thumb_path, media_type="image/jpeg", headers=UPLOAD_RESPONSE_HEADERS)
            except Exception as e:
                logger.warning(f"Thumbnail generation failed for {file_id}: {e}")
                # Fall through to the full image.
-        return FileResponse(path, media_type=mime, filename=original_name)
+        return FileResponse(
+            path,
+            media_type=mime,
+            filename=original_name,
+            headers=UPLOAD_RESPONSE_HEADERS,
+        )

    def _load_upload_info(file_id: str):
        """Look up the uploads.json record for a file_id, with owner/auth checks."""
-        from src.constants import UPLOAD_DIR
        info = None
-        uploads_db = os.path.join(UPLOAD_DIR, "uploads.json")
+        uploads_db = os.path.join(_upload_root(), "uploads.json")
        if os.path.exists(uploads_db):
            with open(uploads_db, encoding="utf-8") as f:
                db = json.load(f)
@@ -163,8 +190,7 @@ def setup_upload_routes(upload_handler):
        return info

    def _vision_cache_path(file_id: str) -> str:
-        from src.constants import UPLOAD_DIR
-        cache_dir = os.path.join(UPLOAD_DIR, ".vision")
+        cache_dir = os.path.join(_upload_root(), ".vision")
        os.makedirs(cache_dir, exist_ok=True)
        return os.path.join(cache_dir, file_id + ".txt")

@@ -175,17 +201,6 @@ def setup_upload_routes(upload_handler):
        subsequent loads are instant. Pass force=1 to recompute."""
        if not upload_handler.validate_upload_id(file_id):
            raise HTTPException(400, "Invalid file ID")
-        from src.constants import UPLOAD_DIR
-        path = os.path.join(UPLOAD_DIR, file_id)
-        if not os.path.exists(path):
-            for root, dirs, files in os.walk(UPLOAD_DIR):
-                if file_id in files:
-                    path = os.path.join(root, file_id)
-                    break
-            else:
-                raise HTTPException(404, "File not found")
-        if not upload_handler.inside_base_dir(path):
-            raise HTTPException(403, "Access denied")
        info = _load_upload_info(file_id)
        auth_mgr = getattr(request.app.state, "auth_manager", None)
        auth_configured = bool(auth_mgr and auth_mgr.is_configured)
@@ -196,8 +211,9 @@ def setup_upload_routes(upload_handler):
                raise HTTPException(403, "Access denied")
            if file_owner != current_user and not auth_mgr.is_admin(current_user):
                raise HTTPException(404, "File not found")
+        path = _resolve_upload_path(file_id)
        import mimetypes as _mt
-        mime = _mt.guess_type(path)[0] or ""
+        mime = (info or {}).get("mime") or _mt.guess_type(path)[0] or ""
        if not mime.startswith("image/"):
            raise HTTPException(400, "Not an image")
        cache_path = _vision_cache_path(file_id)
@@ -209,7 +225,7 @@ def setup_upload_routes(upload_handler):
                logger.warning(f"Vision cache read failed for {file_id}: {e}")
        from src.document_processor import analyze_image_with_vl
        try:
-            text = analyze_image_with_vl(path) or ""
+            text = analyze_image_with_vl(path, owner=current_user) or ""
        except Exception as e:
            logger.error(f"Vision analysis failed for {file_id}: {e}")
            raise HTTPException(500, f"Vision analysis failed: {e}")
@@ -238,6 +254,7 @@ def setup_upload_routes(upload_handler):
                raise HTTPException(403, "Access denied")
            if file_owner != current_user and not auth_mgr.is_admin(current_user):
                raise HTTPException(404, "File not found")
+        _resolve_upload_path(file_id)
        body = await request.json()
        text = (body or {}).get("text", "")
        if not isinstance(text, str):
@@ -17,10 +17,11 @@ from pydantic import BaseModel

 from core.middleware import require_admin
 from core.platform_compat import IS_WINDOWS, safe_chmod, which_tool
+from src.constants import VAULT_FILE as _VAULT_FILE

 logger = logging.getLogger(__name__)

-VAULT_FILE = Path("data/vault.json")
+VAULT_FILE = Path(_VAULT_FILE)


 def _find_bw() -> str:
@@ -194,6 +194,8 @@ def setup_webhook_routes(
        "together": "https://api.together.xyz/v1",
        "openrouter": "https://openrouter.ai/api/v1",
        "ollama": "https://ollama.com/api",
+        "opencode-zen": "https://opencode.ai/zen/v1",
+        "opencode-go": "https://opencode.ai/zen/go/v1",
        "fireworks": "https://api.fireworks.ai/inference/v1",
        "venice": "https://api.venice.ai/api/v1",
    }
@@ -323,22 +325,33 @@ def setup_webhook_routes(
            endpoint_url = build_chat_url(base_url)
            model = body.model or "auto"
            api_key = ep.api_key
+            if getattr(ep, "provider_auth_id", None):
+                try:
+                    from src.endpoint_resolver import resolve_endpoint_runtime
+                    base_url, api_key = resolve_endpoint_runtime(ep, owner=token_owner)
+                    endpoint_url = build_chat_url(base_url)
+                except Exception:
+                    raise HTTPException(500, "Could not resolve endpoint credentials")

            if model == "auto":
                try:
                    async with httpx.AsyncClient(timeout=5) as client:
                        models_url = build_models_url(base_url)
                        hdrs = build_headers(api_key, base_url)
-                        resp = await client.get(models_url, headers=hdrs)
-                        resp.raise_for_status()
-                        data = resp.json()
-                        ids = [m.get("id") for m in (data.get("data") or []) if m.get("id")]
-                        if not ids:
-                            ids = [
-                                m.get("name") or m.get("model")
-                                for m in (data.get("models") or [])
-                                if m.get("name") or m.get("model")
-                            ]
+                        if models_url:
+                            resp = await client.get(models_url, headers=hdrs)
+                            resp.raise_for_status()
+                            data = resp.json()
+                            ids = [m.get("id") for m in (data.get("data") or []) if m.get("id")]
+                            if not ids:
+                                ids = [
+                                    m.get("name") or m.get("model")
+                                    for m in (data.get("models") or [])
+                                    if m.get("name") or m.get("model")
+                                ]
+                        else:
+                            import json as _json
+                            ids = _json.loads(ep.cached_models or "[]")
                        model = ids[0] if ids else "auto"
                except Exception:
                    raise HTTPException(500, "Could not discover models from endpoint")
@@ -1,56 +0,0 @@
-"""Workspace API — browse server directories to pick a tool workspace folder."""
-import os
-from fastapi import APIRouter, Request, HTTPException, Query
-
-from src.auth_helpers import get_current_user
-from src.tool_security import owner_is_admin_or_single_user
-
-
-def setup_workspace_routes():
-    router = APIRouter(prefix="/api/workspace", tags=["workspace"])
-
-    @router.get("/browse")
-    def browse(request: Request, path: str = Query(default="")):
-        """List subdirectories of `path` (default: home) so the UI can navigate
-        the server filesystem and pick a workspace folder. Directories only.
-
-        ADMIN-ONLY: this enumerates the server filesystem, so it is gated the
-        same way the file/shell tools are (read_file/write_file/bash are in
-        NON_ADMIN_BLOCKED_TOOLS). A non-admin who can't use those tools must not
-        be able to map the host's directory tree either.
-        """
-        owner = get_current_user(request)
-        if not owner_is_admin_or_single_user(owner):
-            raise HTTPException(status_code=403, detail="Workspace browsing is admin-only")
-
-        # Resolve symlinks so the reported path is canonical and the UI navigates
-        # real directories (defends against symlink games in displayed paths).
-        target = os.path.realpath(os.path.expanduser(path.strip() or "~"))
-        if not os.path.isdir(target):
-            target = os.path.realpath(os.path.expanduser("~"))
-
-        dirs = []
-        try:
-            with os.scandir(target) as it:
-                for entry in it:
-                    try:
-                        # Don't follow symlinks when classifying — a symlinked
-                        # dir is skipped rather than letting the browser wander
-                        # off via a link. Hidden entries are omitted.
-                        if entry.is_dir(follow_symlinks=False) and not entry.name.startswith("."):
-                            # Build the child path server-side with os.path.join
-                            # so it's correct on Windows (backslashes) and Linux.
-                            dirs.append({"name": entry.name, "path": os.path.join(target, entry.name)})
-                    except OSError:
-                        continue
-        except (PermissionError, OSError):
-            dirs = []
-
-        parent = os.path.dirname(target)
-        return {
-            "path": target,
-            "parent": parent if parent and parent != target else None,
-            "dirs": sorted(dirs, key=lambda d: d["name"].lower()),
-        }
-
-    return router
@@ -13,6 +13,8 @@ import json

 sys.path.insert(0, os.path.dirname(os.path.dirname(os.path.abspath(__file__))))

+from src.constants import MEMORY_FILE, SKILLS_FILE
+

 def claim_json_entries(entries, owner):
    count = 0
@@ -35,8 +37,8 @@ def main():

    # 1. Memories (JSON files)
    for label, path in [
-        ("memory.json", "data/memory.json"),
-        ("skills.json", "data/skills.json"),
+        ("memory.json", MEMORY_FILE),
+        ("skills.json", SKILLS_FILE),
    ]:
        if not os.path.exists(path):
            print(f"  {label}: not found, skipping")
@@ -34,6 +34,7 @@ import torch
 import uvicorn
 from fastapi import FastAPI
 from fastapi.middleware.cors import CORSMiddleware
+from starlette.middleware.trustedhost import TrustedHostMiddleware
 from pydantic import BaseModel

 logging.basicConfig(level=logging.INFO)
@@ -52,7 +53,63 @@ async def lifespan(application):


 app = FastAPI(title="Diffusion Server", lifespan=lifespan)
-app.add_middleware(CORSMiddleware, allow_origins=["*"], allow_methods=["*"], allow_headers=["*"])
+
+# Conservative defaults — server is designed for server-to-server use from
+# the Odysseus backend. Wildcard CORS + the 127.0.0.1 default bind used to
+# leave the server reachable via DNS-rebinding from any browser tab on the
+# same host. The CLI flags below extend these allowlists for operators who
+# need browser access; the safe defaults handle the common case.
+_DEFAULT_ALLOWED_HOSTS = ["127.0.0.1", "localhost", "::1"]
+_DEFAULT_CORS_ORIGINS: list = []  # default-deny
+
+
+def _compute_allowed_hosts(bind_host: str, extras=None) -> list:
+    """Allowed Host header values: the bind address + loopback variants +
+    any operator-supplied --allowed-host values. Duplicates and empty
+    strings are dropped; order is stable for predictable middleware setup."""
+    seen = []
+    for h in (bind_host, *_DEFAULT_ALLOWED_HOSTS, *(extras or [])):
+        h = (h or "").strip()
+        if h and h not in seen:
+            seen.append(h)
+    return seen
+
+
+def _compute_cors_origins(extras=None) -> list:
+    """CORS allowlist: default-deny (empty), extended only by explicit
+    --allowed-origin values. Server-to-server callers don't set an Origin
+    header so they're unaffected; this only narrows browser access."""
+    seen = []
+    for o in (*_DEFAULT_CORS_ORIGINS, *(extras or [])):
+        o = (o or "").strip()
+        if o and o not in seen:
+            seen.append(o)
+    return seen
+
+
+def _configure_security_middleware(application, allowed_hosts, allowed_origins):
+    """Replace `application`'s user middleware stack with the diffusion server
+    security middleware: the TrustedHost allowlist and, when origins are
+    supplied, CORS. Used at module load and by the __main__ CLI path before
+    serving starts. Raises before mutating if the middleware stack has already
+    been built. Order is preserved: TrustedHost first, then CORS (added last ->
+    outermost)."""
+    if application.middleware_stack is not None:
+        raise RuntimeError("security middleware must be configured before the app starts serving")
+    application.user_middleware.clear()
+    application.add_middleware(TrustedHostMiddleware, allowed_hosts=list(allowed_hosts))
+    if allowed_origins:
+        application.add_middleware(
+            CORSMiddleware,
+            allow_origins=list(allowed_origins),
+            allow_methods=["GET", "POST", "OPTIONS"],
+            allow_headers=["Authorization", "Content-Type"],
+        )
+
+
+# Install defaults at module load so importing the app for tests / direct
+# uvicorn invocation still benefits from the Host-header allowlist.
+_configure_security_middleware(app, _DEFAULT_ALLOWED_HOSTS, _DEFAULT_CORS_ORIGINS)


 class ImageRequest(BaseModel):
@@ -1089,7 +1146,25 @@ if __name__ == "__main__":
    parser.add_argument("--attention-slicing", action="store_true", help="Enable attention slicing")
    parser.add_argument("--vae-slicing", action="store_true", help="Enable VAE slicing")
    parser.add_argument("--harmonize-gpu", type=int, default=None, help="GPU index for harmonize/img2img (default: same as main)")
+    parser.add_argument("--allowed-host", action="append", default=[],
+        help="Additional Host header value to accept (DNS-rebinding allowlist). "
+             "Can be repeated. Loopback values are always included.")
+    parser.add_argument("--allowed-origin", action="append", default=[],
+        help="Additional CORS origin to allow. Can be repeated. Defaults to "
+             "no cross-origin access — only pass this if you need a browser "
+             "on a specific origin to call the server.")
    _args = parser.parse_args()

+    # Replace the module-load middleware stack with the CLI-configured one so
+    # operator-supplied --allowed-host / --allowed-origin values take effect
+    # before the first request is served. user_middleware is consulted lazily
+    # when the middleware stack is built on the first request, so mutating it
+    # here is safe.
+    final_hosts = _compute_allowed_hosts(_args.host, _args.allowed_host)
+    final_origins = _compute_cors_origins(_args.allowed_origin)
+    _configure_security_middleware(app, final_hosts, final_origins)
+    logger.info("security middleware: allowed_hosts=%s allowed_origins=%s",
+                final_hosts, final_origins or "(none — default-deny)")
+
    app.state.model_path = _args.model
    uvicorn.run(app, host=_args.host, port=_args.port)
@@ -19,6 +19,9 @@ import sys
 from pathlib import Path
 from typing import List, Tuple

+sys.path.insert(0, os.path.dirname(os.path.dirname(os.path.abspath(__file__))))
+from src.constants import PERSONAL_DIR
+
 # Configure logging for the script
 logging.basicConfig(
    level=logging.INFO,
@@ -45,7 +48,7 @@ def main():
    rag_manager = RAGManager()
    
    # Directory to scan
-    docs_directory = "data/personal_docs"
+    docs_directory = PERSONAL_DIR
    directory_path = Path(docs_directory)
    
    # Check if directory exists
@@ -63,10 +63,10 @@ def migrate_memories():
    """Migrate memory vectors from FAISS to ChromaDB."""
    from src.chroma_client import get_chroma_client
    from src.embeddings import get_embedding_client
-    from src.constants import DATA_DIR
+    from src.constants import MEMORY_VECTORS_DIR, MEMORY_FILE

-    ids_path = os.path.join(DATA_DIR, "memory_vectors", "ids.json")
-    memory_path = os.path.join(DATA_DIR, "memory.json")
+    ids_path = os.path.join(MEMORY_VECTORS_DIR, "ids.json")
+    memory_path = MEMORY_FILE

    if not os.path.exists(ids_path):
        logger.info("No memory FAISS index found, skipping memory migration")
@@ -47,6 +47,9 @@ _STATE_PATH = _DATA_DIR / "cookbook_state.json"
 import tempfile
 _TMUX_LOG_DIR = Path(tempfile.gettempdir()) / "odysseus-tmux"

+from core.platform_compat import NVIDIA_PATH_CANDIDATES, SSH_PATH_OVERRIDE
+
+

 def fail(msg: str, code: int = 1) -> None:
    sys.stderr.write(f"error: {msg}\n")
@@ -160,7 +163,26 @@ def cmd_gpus(args) -> None:
    prefix = _ssh_prefix(args.host, args.ssh_port)
    cmd = prefix + (query.split() if not prefix else [query])
    try:
-        out = subprocess.run(cmd, capture_output=True, text=True, timeout=15)
+        if prefix:
+            candidates = [query]
+            args_part = query[len("nvidia-smi "):]
+            candidates.append(
+                "bash -lc "
+                + repr(
+                    f"{SSH_PATH_OVERRIDE}"
+                    f"nvidia-smi {args_part}"
+                )
+            )
+            for nvidia_path in NVIDIA_PATH_CANDIDATES:
+                candidates.append(f"{nvidia_path} {args_part}")
+
+            out = None
+            for candidate in candidates:
+                out = subprocess.run(prefix + [candidate], capture_output=True, text=True, timeout=15)
+                if out.returncode == 0:
+                    break
+        else:
+            out = subprocess.run(cmd, capture_output=True, text=True, timeout=15)
    except FileNotFoundError:
        # No nvidia-smi locally → try the Metal fallback before giving up.
        if not prefix:
@@ -25,6 +25,24 @@ from pathlib import Path

 _DATA_DIR = _REPO_ROOT / "data" / "deep_research"

+# The CLI's --status takes the user-facing label "complete", but the writer
+# in services/research/research_handler.py stores `status="done"` when a run
+# finishes (and the legacy src/research_handler.py does the same). Without
+# this alias, --status complete filters every finished record out and the
+# user sees an empty list. Map at filter time so the on-disk corpus is the
+# source of truth and the CLI surface stays the friendlier word. The other
+# choices ("running", "cancelled", "error") are stored verbatim, so they
+# fall through unchanged.
+_STATUS_CLI_TO_STORED = {"complete": "done"}
+
+
+def _status_matches(stored, requested: str) -> bool:
+    stored = (stored or "")
+    if not isinstance(stored, str):
+        stored = ""
+    target = _STATUS_CLI_TO_STORED.get(requested, requested)
+    return stored == target
+

 def _load_path(path: Path) -> dict | None:
    try:
@@ -72,7 +90,7 @@ def cmd_list(args):
        data = _load_path(path)
        if data is None:
            continue
-        if args.status and (data.get("status") or "") != args.status:
+        if args.status and not _status_matches(data.get("status"), args.status):
            continue
        out.append(_summarize(rp_id, data))
    out.sort(key=lambda r: r.get("started_at") or "", reverse=True)
@@ -5,6 +5,7 @@ from dataclasses import dataclass
 from typing import List, Dict, Any

 from src.rag_manager import RAGManager
+from src.constants import CHROMA_DIR


@dataclass
@@ -34,7 +35,7 @@ class DocsService:
        results = await service.query("what is async await?")
    """

-    def __init__(self, persist_dir: str = "data/chroma"):
+    def __init__(self, persist_dir: str = CHROMA_DIR):
        self.rag = RAGManager(persist_directory=persist_dir)

    async def query(self, query: str, top_k: int = 5) -> List[DocChunk]:
@@ -14036,6 +14036,29 @@
   "vision"
  ]
 },
+ {
+  "name": "google/gemma-4-12B",
+  "provider": "Google",
+  "parameter_count": "12.0B",
+  "parameters_raw": 12000000000,
+  "min_ram_gb": 24.0,
+  "recommended_ram_gb": 32.0,
+  "min_vram_gb": 24.0,
+  "quantization": "BF16",
+  "context_length": 131072,
+  "use_case": "General purpose, multimodal",
+  "is_moe": false,
+  "num_experts": null,
+  "active_experts": null,
+  "active_parameters": null,
+  "architecture": "gemma4",
+  "pipeline_tag": "image-text-to-text",
+  "release_date": "2026-04-01",
+  "gguf_sources": [],
+  "capabilities": [
+   "vision"
+  ]
+ },
 {
  "name": "google/gemma-4-31B-it",
  "provider": "Google",
@@ -19121,4 +19144,4 @@
  ],
  "_discovered": true
 }
-]
+]
@@ -4,6 +4,13 @@ import re
 import shutil
 import subprocess
 import time
+import shlex
+
+from core.platform_compat import (
+    NVIDIA_PATH_CANDIDATES,
+    SSH_PATH_OVERRIDE,
+    run_ssh_command,
+)

 CACHE_TTL = 24 * 3600  # 24 h — hardware probes are user-initiated via the Rescan button; bumped
                       # from 30 min so changing filters doesn't keep re-probing the rig every
@@ -21,16 +28,17 @@ def _run(cmd):
        if _remote_host:
            # Run command on remote host via SSH
            if isinstance(cmd, list):
-                cmd_str = " ".join(cmd)
+                cmd_str = shlex.join(str(c) for c in cmd)
            else:
                cmd_str = cmd
-            ssh_cmd = ["ssh", "-o", "ConnectTimeout=5", "-o", "StrictHostKeyChecking=no"]
-            if _remote_port and _remote_port != "22":
-                ssh_cmd += ["-p", _remote_port]
-            ssh_cmd += [_remote_host, cmd_str]
-            r = subprocess.run(
-                ssh_cmd,
-                capture_output=True, text=True, timeout=15,
+            r = run_ssh_command(
+                _remote_host,
+                _remote_port,
+                cmd_str,
+                timeout=15,
+                connect_timeout=5,
+                strict_host_key_checking=False,
+                text=True,
            )
        else:
            r = subprocess.run(cmd, capture_output=True, text=True, timeout=10)
@@ -76,21 +84,29 @@ def _detect_nvidia():
    global _last_gpu_error
    _last_gpu_error = None
    out = _run(["nvidia-smi", "--query-gpu=memory.total,name", "--format=csv,noheader,nounits"])
-    # Remote fallback: a non-interactive SSH shell often has a minimal PATH
-    # that omits where nvidia-smi lives (/usr/bin, /usr/local/cuda/bin), so the
-    # first call silently returns nothing → "No GPU" on hosts that DO have GPUs.
+    # Fallback: a non-interactive shell (or WSL) often has a minimal PATH
+    # that omits where nvidia-smi lives (/usr/bin, /usr/local/cuda/bin,
+    # /usr/lib/wsl/lib), so the first call silently returns nothing →
+    # "No GPU" on machines that DO have GPUs.
    # Retry through a login shell with the common CUDA bin dirs on PATH.
    if not out and _remote_host:
        out = _run(
-            "bash -lc 'export PATH=\"$PATH:/usr/bin:/usr/local/bin:/usr/local/cuda/bin\"; "
+            f"bash -lc '{SSH_PATH_OVERRIDE}"
            "nvidia-smi --query-gpu=memory.total,name --format=csv,noheader,nounits'"
        )
    # Last resort: call nvidia-smi by absolute path. Some hosts have a login
    # shell that isn't bash (or a profile that errors), so the bash -lc retry
    # above still comes back empty even though the binary is right there.
-    if not out and _remote_host:
-        for _p in ("/usr/bin/nvidia-smi", "/usr/local/bin/nvidia-smi", "/usr/local/cuda/bin/nvidia-smi"):
-            out = _run(f"{_p} --query-gpu=memory.total,name --format=csv,noheader,nounits")
+    # Also handles WSL where nvidia-smi lives at /usr/lib/wsl/lib/ — a path
+    # that may not be in the server process's PATH.
+    if not out:
+        for _p in NVIDIA_PATH_CANDIDATES:
+            # Use list form so subprocess.run (local) resolves the absolute path
+            # correctly instead of treating the whole string as an executable name.
+            if _remote_host:
+                out = _run(f"{_p} --query-gpu=memory.total,name --format=csv,noheader,nounits")
+            else:
+                out = _run([_p, "--query-gpu=memory.total,name", "--format=csv,noheader,nounits"])
            if out:
                break
    if not out:
@@ -468,39 +484,55 @@ def _detect_windows():
    """
    # Single PowerShell command that gathers all hardware info at once
    ps_cmd = (
-        "$r = @{}; "
-        "$os = Get-CimInstance Win32_OperatingSystem; "
-        "$r.ram_gb = [math]::Round($os.TotalVisibleMemorySize / 1048576, 1); "
-        "$r.avail_gb = [math]::Round($os.FreePhysicalMemory / 1048576, 1); "
-        "$cpu = Get-CimInstance Win32_Processor | Select-Object -First 1; "
-        "$r.cpu_name = $cpu.Name; "
-        "$r.cpu_cores = (Get-CimInstance Win32_Processor | Measure-Object -Property NumberOfLogicalProcessors -Sum).Sum; "
-        "$r.arch = $cpu.AddressWidth; "
+        """
+        $r = @{}
+        $os = Get-CimInstance Win32_OperatingSystem
+        $r.ram_gb = [math]::Round($os.TotalVisibleMemorySize / 1048576, 1)
+        $r.avail_gb = [math]::Round($os.FreePhysicalMemory / 1048576, 1)
+        $cpu = Get-CimInstance Win32_Processor | Select-Object -First 1
+        $r.cpu_name = $cpu.Name
+        $r.cpu_cores = (Get-CimInstance Win32_Processor | Measure-Object -Property NumberOfLogicalProcessors -Sum).Sum
+        $r.arch = $cpu.AddressWidth
        # GPU detection via nvidia-smi (fastest) or WMI fallback
-        "try { "
-        "  $nv = nvidia-smi --query-gpu=memory.total,name --format=csv,noheader,nounits 2>$null; "
-        "  if ($LASTEXITCODE -eq 0 -and $nv) { "
-        "    $gpus = @(); "
-        "    foreach ($line in $nv -split \"`n\") { "
-        "      $p = $line -split ','; "
-        "      if ($p.Count -ge 2) { $gpus += [pscustomobject]@{name=$p[1].Trim(); vram_mb=[double]$p[0].Trim()} } "
-        "    }; "
-        "    $r.gpu_name = $gpus[0].name; "
-        "    $r.gpu_vram_gb = [math]::Round(($gpus | Measure-Object -Property vram_mb -Sum).Sum / 1024, 1); "
-        "    $r.gpu_count = $gpus.Count; "
-        "    $r.gpu_backend = 'cuda'; "
-        "  } "
-        "} catch {}; "
-        "if (-not $r.gpu_name) { "
-        "  $wmiGpu = Get-CimInstance Win32_VideoController | Where-Object { $_.AdapterRAM -gt 0 } | Select-Object -First 1; "
-        "  if ($wmiGpu) { "
-        "    $r.gpu_name = $wmiGpu.Name; "
-        "    $r.gpu_vram_gb = [math]::Round($wmiGpu.AdapterRAM / 1073741824, 1); "
-        "    $r.gpu_count = 1; "
-        "    $r.gpu_backend = 'cpu_x86'; "  # WMI doesn't tell us CUDA/ROCm
-        "  } "
-        "}; "
-        "$r | ConvertTo-Json -Compress"
+        try { 
+            $nv = nvidia-smi --query-gpu=memory.total,name --format=csv,noheader,nounits 2>$null
+            if ($LASTEXITCODE -eq 0 -and $nv) { 
+                $gpus = @()
+                foreach ($line in $nv -split "`n") { 
+                    $p = $line -split ','
+                    if ($p.Count -ge 2) { $gpus += [pscustomobject]@{name = $p[1].Trim(); vram_mb = [double]$p[0].Trim() } } 
+                }
+                $r.gpu_name = $gpus[0].name
+                $r.gpu_vram_gb = [math]::Round(($gpus | Measure-Object -Property vram_mb -Sum).Sum / 1024, 1)
+                $r.gpu_count = $gpus.Count
+                $r.gpu_backend = 'cuda'
+            } 
+        }
+        catch {}
+        if (-not $r.gpu_name) { 
+            $wmiGpu = Get-CimInstance Win32_VideoController | Where-Object { $_.AdapterRAM -gt 0 } | Select-Object -First 1
+            $GPUDriverKey = "HKLM:\\SYSTEM\\CurrentControlSet\\Control\\Class\\{4d36e968-e325-11ce-bfc1-08002be10318}\\0*"
+            $GPUDeviceID = $wmiGpu.PNPDeviceID.Split('&')[0..1] -join '&'
+            $VRAMfromRegistry = Get-ItemProperty -Path $GPUDriverKey |
+            Where-Object { $_.MatchingDeviceId -like "${GPUDeviceID}*" } |
+            # Sometimes there happen to be multiple driver classes for the same gpu.
+            Select-Object -ExpandProperty HardwareInformation.qwMemorySize -ErrorAction SilentlyContinue -First 1
+            if ($wmiGpu) { 
+                $r.gpu_name = $wmiGpu.Name
+                # Edge case: driver is broken, otherwise $wmiGpu.AdapterRAM is redundant
+                if ($VRAMfromRegistry -ge $wmiGpu.AdapterRAM) {
+                    $r.gpu_vram_gb = [math]::Round($VRAMfromRegistry / 1073741824, 1)
+                }
+                else {
+                    $r.gpu_vram_gb = [math]::Round($wmiGpu.AdapterRAM / 1073741824, 1)
+                }
+                $r.gpu_count = 1
+                # WMI doesn't tell us CUDA/ROCm
+                $r.gpu_backend = 'cpu_x86';
+            } 
+        }
+        $r | ConvertTo-Json -Compress
+    """
    )
    if _remote_host:
        # Remote: ship a single command string over SSH. The remote shell parses
@@ -566,6 +598,19 @@ def _detect_windows():
 _cache_by_host = {}  # host -> (timestamp, result)


+def _cache_key(host: str, ssh_port: str, platform_name: str):
+    """Build a stable cache key that isolates remote SSH context.
+
+    Same host aliases can have different hardware due to visibility, forwarding etc.
+    To avoid using the wrong cached hardware info, include the SSH port and platform in the cache key.
+    """
+    return (
+        host or "_local",
+        str(ssh_port or ""),
+        str(platform_name or "").lower(),
+    )
+
+
 def detect_system(host="", ssh_port="", platform="", fresh=False):
    """Detect system hardware: RAM, CPU, GPU. Cached per host (hardware rarely
    changes, and probing a remote host over SSH is slow). Pass fresh=True to
@@ -575,7 +620,7 @@ def detect_system(host="", ssh_port="", platform="", fresh=False):
    """
    global _remote_host, _remote_port, _remote_platform

-    cache_key = host or "_local"
+    cache_key = _cache_key(host, ssh_port, platform)
    now = time.time()
    if not fresh and cache_key in _cache_by_host:
        ts, cached = _cache_by_host[cache_key]
@@ -192,11 +192,19 @@ def _fallback_memory_candidates(messages) -> list[dict]:
            if place:
                add(f"User lives in {place}.", "identity")

-        m = re.search(r"\bi (?:prefer|like|love|hate|do not like|don't like)\s+([^.!?\n]{4,100})", text, re.I)
+        m = re.search(r"\bi (prefer|like|love|hate|do not like|don't like)\s+([^.!?\n]{4,100})", text, re.I)
        if m:
-            preference = _clean_memory_value(m.group(1), 100)
+            preference = _clean_memory_value(m.group(2), 100)
            if preference:
-                add(f"User prefers {preference}.", "preference")
+                # The same pattern catches likes and dislikes; keep the stored
+                # sentiment faithful instead of recording every match as a
+                # preference ("I hate cilantro" must not become "User prefers
+                # cilantro").
+                verb = m.group(1).lower()
+                if verb in ("hate", "do not like", "don't like"):
+                    add(f"User dislikes {preference}.", "preference")
+                else:
+                    add(f"User prefers {preference}.", "preference")

        m = re.search(
            r"\bi (?:(?:want|would like|plan|hope) to|wanna) "
@@ -228,6 +236,43 @@ def _is_text_duplicate(new_text: str, existing: list, threshold: float = 0.6) ->
    return False


+def _parse_extraction_json(raw: str) -> list:
+    """Parse the extraction LLM's reply into a list of facts, tolerating
+    reasoning-model noise.
+
+    The model emits <think>…</think> (and sometimes a prose preamble or a
+    ```json fence) AROUND the JSON array; without stripping it, json.loads
+    bombs and the run silently yields "0 candidates". Pure str -> list (no
+    LLM/network); returns [] on any parse failure instead of raising.
+    """
+    text = (raw or "").strip()
+    try:
+        from src.text_helpers import strip_think as _strip_think
+        text = _strip_think(text, prose=True, prompt_echo=True).strip()
+    except Exception:
+        pass
+    if text.startswith("```"):
+        text = text.split("\n", 1)[-1].rsplit("```", 1)[0].strip()
+    # JSON may still be embedded in surrounding commentary (leading prose or
+    # trailing remarks like "[...] Done!") — slice from the first '[' to the
+    # last ']' whenever both exist. Slice unconditionally: a reply that starts
+    # with '[' can still carry trailing commentary that breaks json.loads.
+    _start = text.find("[")
+    _end = text.rfind("]")
+    if 0 <= _start < _end:
+        text = text[_start : _end + 1]
+
+    try:
+        facts = json.loads(text)
+    except json.JSONDecodeError:
+        logger.debug("Memory extraction returned non-JSON: %r", (raw or "")[:120])
+        return []
+    except Exception:
+        logger.debug("Memory extraction returned non-JSON: %r", (raw or "")[:120])
+        return []
+    return facts if isinstance(facts, list) else []
+
+
 async def extract_and_store(
    session,
    memory_manager,
@@ -276,9 +321,34 @@ async def extract_and_store(

        fallback_facts = _fallback_memory_candidates(stripped_recent)

+        # Flatten the window into a SINGLE user message instead of appending the
+        # raw alternating role messages. Passed as raw chat messages, the model
+        # treats the window as a conversation to CONTINUE rather than a transcript
+        # to ANALYZE, so it reliably extracts nothing — typically returning `[]`
+        # (and, depending on the input, sometimes an empty or <think>-only
+        # completion when the window ends on an assistant turn). This was the real
+        # cause of auto-memory logging "0 candidates" on every run. Reframing it as
+        # one "analyze this transcript, return the JSON array" user message makes
+        # the model actually extract. Controlled repro on this model: 0/6 trials
+        # with the old structure vs 6/6 with this one. The skill extractor flattens
+        # for the same reason.
+        def _flatten_msg(m):
+            c = m.get("content", "")
+            if isinstance(c, list):
+                c = " ".join(
+                    b.get("text", "") for b in c
+                    if isinstance(b, dict) and b.get("type") == "text"
+                )
+            return f"{m.get('role', '?')}: {c}"
+
+        transcript = "\n\n".join(_flatten_msg(m) for m in stripped_recent)
        extraction_messages = [
            {"role": "system", "content": EXTRACT_SYSTEM_PROMPT},
-        ] + stripped_recent
+            {"role": "user", "content": (
+                "Conversation to analyze:\n\n" + transcript
+                + "\n\nReturn the JSON array of durable facts now (or [] if none)."
+            )},
+        ]

        facts = []
        try:
@@ -287,19 +357,20 @@ async def extract_and_store(
                model,
                extraction_messages,
                temperature=0.1,
-                max_tokens=500,
+                # A reasoning model spends most of its budget on <think> tokens
+                # BEFORE emitting the JSON, so the old 500 truncated the response
+                # before any JSON appeared → every run logged "0 candidates". The
+                # audit path hit the same wall and raised to 16384; extraction's
+                # output (a short facts list) is small, so an ample ceiling is
+                # enough once thinking has room.
+                max_tokens=4096,
                headers=headers,
            )

-            # Parse JSON from response (handle markdown fences if model wraps them)
-            text = raw.strip()
-            if text.startswith("```"):
-                text = text.split("\n", 1)[-1].rsplit("```", 1)[0].strip()
-
-            try:
-                facts = json.loads(text)
-            except json.JSONDecodeError:
-                logger.debug("Memory extraction returned non-JSON")
+            # Parse JSON, tolerating reasoning-model noise (<think> blocks, a
+            # ```json fence, and leading/trailing commentary). See
+            # _parse_extraction_json — returns [] rather than raising.
+            facts = _parse_extraction_json(raw)
        except Exception as e:
            logger.warning(f"LLM memory extraction failed; using fallback candidates if available: {e}")

@@ -8,6 +8,7 @@ import os
 from .memory import MemoryManager
 from .memory_vector import MemoryVectorStore
 from src.memory_provider import MemoryRecord, NativeMemoryProvider
+from src.constants import DATA_DIR


@dataclass
@@ -38,7 +39,7 @@ class MemoryService:
        results = await service.recall("preferences")
    """

-    def __init__(self, data_dir: str = "data"):
+    def __init__(self, data_dir: str = DATA_DIR):
        self.manager = MemoryManager(data_dir)
        self.vector_store = MemoryVectorStore(data_dir) if os.path.exists(
            os.path.join(data_dir, "memory_vectors")
@@ -63,6 +63,46 @@ def _has_duplicate_title(skills, title: str) -> bool:
    return False


+def _extract_json_object(text: str) -> Optional[dict]:
+    """Best-effort extraction of a JSON object from an LLM response.
+
+    The response may be wrapped in code fences or surrounded by prose, and some
+    models emit a stray brace in the prose before the real object
+    (e.g. "uses {placeholder} then {...}"). Slicing first-'{' .. last-'}' then
+    grabs an unparseable span and the skill is silently lost. Try the whole
+    string first, then each '{' start position in turn, returning the first
+    candidate that parses to a JSON object (dict). Returns None if none do.
+    """
+    if not text:
+        return None
+    s = text.strip()
+    if s.startswith("```"):
+        s = s.split("\n", 1)[-1].rsplit("```", 1)[0].strip()
+    end = s.rfind("}")
+    if end == -1:
+        return None
+
+    def _as_dict(candidate):
+        try:
+            obj = json.loads(candidate)
+        except (json.JSONDecodeError, ValueError):
+            return None
+        return obj if isinstance(obj, dict) else None
+
+    # The clean, common case: the whole (de-fenced) string is the object.
+    obj = _as_dict(s)
+    if obj is not None:
+        return obj
+    # Otherwise scan each '{' candidate up to the last '}'.
+    start = s.find("{")
+    while 0 <= start < end:
+        obj = _as_dict(s[start : end + 1])
+        if obj is not None:
+            return obj
+        start = s.find("{", start + 1)
+    return None
+
+
 async def maybe_extract_skill(
    session,
    skills_manager,
@@ -169,21 +209,14 @@ async def maybe_extract_skill(
        except Exception:
            pass

-        # Parse JSON
-        text = response.strip()
-        if text.startswith("```"):
-            text = text.split("\n", 1)[-1].rsplit("```", 1)[0].strip()
-        # After strip_think, the JSON may still be embedded inside surrounding
-        # commentary — slice from the first '{' to the matching last '}'.
-        if text and text[0] != "{":
-            _start = text.find("{")
-            _end = text.rfind("}")
-            if 0 <= _start < _end:
-                text = text[_start : _end + 1]
-
-        data = json.loads(text)
-        if not data or not isinstance(data, dict):
-            logger.debug("[skill-extract] parsed JSON not a dict, dropping")
+        # Parse JSON. The object may be wrapped in code fences or surrounded by
+        # commentary (and may contain a stray/invalid brace fragment before
+        # the real object — including one that makes the response itself look
+        # like it starts with '{'), so use a tolerant extractor that tries the
+        # whole string first and then each '{' candidate left-to-right.
+        data = _extract_json_object(response)
+        if not data:
+            logger.debug("[skill-extract] no JSON object found in response, dropping")
            return None

        title = data.get("title", "").strip()
@@ -210,6 +243,20 @@ async def maybe_extract_skill(
            logger.debug("[skill-extract] '%s' already exists — dropped as duplicate", title)
            return None

+        # Auto-publish gate: if the user has `auto_approve_skills` on, the
+        # newly-extracted skill is created `published` immediately rather
+        # than waiting for the next audit batch. The audit still runs later
+        # and can demote it back to `draft` (or delete) on failure. Default
+        # ON matches the UI label "Auto-approve skills".
+        _initial_status = "draft"
+        try:
+            from routes.prefs_routes import _load_for_user as _load_prefs
+            _prefs = _load_prefs(owner) or {}
+            if _prefs.get("auto_approve_skills", True):
+                _initial_status = "published"
+        except Exception:
+            pass
+
        entry = skills_manager.add_skill(
            title=title,
            problem=data.get("problem", ""),
@@ -220,6 +267,7 @@ async def maybe_extract_skill(
            confidence=data.get("confidence", 0.7),
            session_id=getattr(session, "session_id", None),
            owner=owner,
+            status=_initial_status,
        )
        try:
            from src.event_bus import fire_event
@@ -0,0 +1,283 @@
+"""Import SKILL.md bundles from public GitHub (or skills.sh → GitHub) URLs."""
+from __future__ import annotations
+
+import logging
+import os
+import re
+from dataclasses import dataclass
+from typing import Dict, List, Optional, Tuple
+from urllib.parse import quote, urlparse
+
+import httpx
+
+from src.url_safety import check_outbound_url
+
+logger = logging.getLogger(__name__)
+
+MAX_FILES = 64
+MAX_TOTAL_BYTES = 2_000_000
+MAX_FILE_BYTES = 400_000
+ALLOWED_SUFFIXES = (
+    ".md", ".txt", ".json", ".yaml", ".yml", ".py", ".sh", ".toml",
+    ".js", ".ts", ".css", ".html", ".xml", ".csv",
+)
+TEXT_NAMES = {"skill.md", "license", "license.md", "readme.md"}
+_GITHUB_HOSTS = frozenset({
+    "github.com", "www.github.com", "api.github.com", "raw.githubusercontent.com",
+})
+
+
+def _github_host(url: str) -> str:
+    return (urlparse(str(url)).hostname or "").lower()
+
+
+def _assert_github_url(url: str, *, context: str = "URL") -> None:
+    host = _github_host(url)
+    if host not in _GITHUB_HOSTS:
+        raise SkillImportError(
+            f"{context} must stay on GitHub (got {host or 'unknown host'})"
+        )
+
+
+@dataclass
+class ResolvedSource:
+    owner: str
+    repo: str
+    ref: str
+    path: str  # directory or file path inside repo (no leading slash)
+
+
+class SkillImportError(ValueError):
+    pass
+
+
+def _safe_relpath(rel: str) -> str:
+    rel = (rel or "").replace("\\", "/").strip().lstrip("/")
+    if not rel or rel.startswith("..") or "/../" in f"/{rel}/":
+        raise SkillImportError(f"unsafe path: {rel!r}")
+    parts = [p for p in rel.split("/") if p and p != "."]
+    if any(p == ".." for p in parts):
+        raise SkillImportError(f"unsafe path: {rel!r}")
+    return "/".join(parts)
+
+
+def _is_text_file(name: str) -> bool:
+    low = name.lower()
+    if low in TEXT_NAMES:
+        return True
+    return any(low.endswith(s) for s in ALLOWED_SUFFIXES)
+
+
+def parse_skill_source(url: str) -> ResolvedSource:
+    """Normalize skills.sh / GitHub web URLs into owner/repo/ref/path."""
+    raw = (url or "").strip()
+    if not raw:
+        raise SkillImportError("URL is required")
+
+    # skills.sh often links to GitHub; try to unwrap ?url= or redirect target later.
+    if "skills.sh" in raw and "github.com" not in raw:
+        ok, reason = check_outbound_url(raw)
+        if not ok:
+            raise SkillImportError(reason)
+        with httpx.Client(follow_redirects=True, timeout=20.0) as client:
+            r = client.get(raw)
+            if r.status_code >= 400:
+                raise _github_response_error(r)
+            final = str(r.url)
+            _assert_github_url(final, context="redirect target")
+            # Page may embed a github link; prefer final URL if redirected.
+            if "github.com" in final:
+                raw = final
+            else:
+                m = re.search(r"https?://github\.com/[^\s\"')]+", r.text or "")
+                if m:
+                    raw = m.group(0).rstrip(".,)")
+
+    parsed = urlparse(raw)
+    host = _github_host(raw)
+    if host not in _GITHUB_HOSTS:
+        raise SkillImportError(
+            "Only GitHub URLs are supported (https://github.com/... or raw.githubusercontent.com/...)"
+        )
+
+    if host == "raw.githubusercontent.com":
+        # /owner/repo/ref/path/to/file
+        bits = [p for p in parsed.path.split("/") if p]
+        if len(bits) < 4:
+            raise SkillImportError("Invalid raw GitHub URL")
+        owner, repo, ref = bits[0], bits[1], bits[2]
+        path = "/".join(bits[3:])
+        return ResolvedSource(owner=owner, repo=repo, ref=ref, path=path)
+
+    bits = [p for p in parsed.path.split("/") if p]
+    if len(bits) < 2:
+        raise SkillImportError("Invalid GitHub URL")
+    owner, repo = bits[0], bits[1]
+    ref = "main"
+    path = ""
+
+    if len(bits) >= 4 and bits[2] in ("tree", "blob"):
+        ref = bits[3]
+        path = "/".join(bits[4:])
+    elif len(bits) == 2:
+        path = ""
+    else:
+        raise SkillImportError("GitHub URL must include /tree/<branch>/... or /blob/<branch>/...")
+
+    return ResolvedSource(owner=owner, repo=repo, ref=ref, path=path)
+
+
+def _raw_url(src: ResolvedSource, rel_path: str) -> str:
+    rel = _safe_relpath(rel_path)
+    return f"https://raw.githubusercontent.com/{src.owner}/{src.repo}/{quote(src.ref, safe='')}/{quote(rel, safe='/')}"
+
+
+def _api_contents_url(src: ResolvedSource, rel_path: str = "") -> str:
+    rel = _safe_relpath(rel_path) if rel_path else ""
+    base = f"https://api.github.com/repos/{src.owner}/{src.repo}/contents"
+    if rel:
+        base += f"/{quote(rel, safe='/')}"
+    return f"{base}?ref={quote(src.ref, safe='')}"
+
+
+def _github_response_error(response: httpx.Response) -> SkillImportError:
+    """Turn a failed GitHub HTTP response into a user-visible import error."""
+    status = response.status_code
+    detail = ""
+    try:
+        body = response.json()
+        if isinstance(body, dict):
+            detail = str(body.get("message") or "").strip()
+    except Exception:
+        detail = (response.text or "").strip()[:200]
+
+    low = detail.lower()
+    if status == 403 and "rate limit" in low:
+        return SkillImportError(
+            "GitHub API rate limit exceeded — try again in a bit"
+            + (f" ({detail})" if detail else "")
+        )
+    if status == 404:
+        return SkillImportError("path not found on GitHub")
+    if detail:
+        return SkillImportError(f"GitHub request failed ({status}): {detail}")
+    return SkillImportError(f"GitHub request failed ({status})")
+
+
+def _fetch_bytes(url: str) -> bytes:
+    ok, reason = check_outbound_url(url)
+    if not ok:
+        raise SkillImportError(reason)
+    with httpx.Client(follow_redirects=True, timeout=30.0) as client:
+        r = client.get(url, headers={"Accept": "application/vnd.github+json"})
+        if r.status_code >= 400:
+            raise _github_response_error(r)
+        _assert_github_url(str(r.url), context="redirect target")
+        if len(r.content) > MAX_FILE_BYTES:
+            raise SkillImportError(f"file too large: {url}")
+        return r.content
+
+
+def _fetch_text(url: str) -> str:
+    data = _fetch_bytes(url)
+    try:
+        return data.decode("utf-8")
+    except UnicodeDecodeError as e:
+        raise SkillImportError(f"non-text file: {url}") from e
+
+
+def _list_github_dir(src: ResolvedSource, rel_dir: str, out: Dict[str, str], *, depth: int = 0) -> None:
+    if depth > 4 or len(out) >= MAX_FILES:
+        return
+    url = _api_contents_url(src, rel_dir)
+    ok, reason = check_outbound_url(url)
+    if not ok:
+        raise SkillImportError(reason)
+    with httpx.Client(follow_redirects=True, timeout=30.0) as client:
+        r = client.get(url, headers={"Accept": "application/vnd.github+json"})
+        if r.status_code >= 400:
+            raise _github_response_error(r)
+        _assert_github_url(str(r.url), context="redirect target")
+        entries = r.json()
+    if not isinstance(entries, list):
+        raise SkillImportError("expected a directory on GitHub")
+    total = sum(len(v.encode("utf-8")) for v in out.values())
+    for ent in entries:
+        if len(out) >= MAX_FILES or total >= MAX_TOTAL_BYTES:
+            break
+        if not isinstance(ent, dict):
+            continue
+        name = ent.get("name") or ""
+        ent_type = ent.get("type")
+        rel = _safe_relpath(f"{rel_dir}/{name}" if rel_dir else name)
+        if ent_type == "dir":
+            _list_github_dir(src, rel, out, depth=depth + 1)
+            total = sum(len(v.encode("utf-8")) for v in out.values())
+            continue
+        if ent_type != "file" or not _is_text_file(name):
+            continue
+        dl = ent.get("download_url")
+        if not dl:
+            continue
+        _assert_github_url(dl, context="download URL")
+        text = _fetch_text(dl)
+        total += len(text.encode("utf-8"))
+        if total > MAX_TOTAL_BYTES:
+            raise SkillImportError("skill bundle exceeds size limit")
+        out[rel] = text
+
+
+def fetch_skill_bundle(url: str) -> Tuple[Dict[str, str], ResolvedSource]:
+    """Download SKILL.md and sibling text assets. Returns relative_path → content."""
+    src = parse_skill_source(url)
+    files: Dict[str, str] = {}
+
+    path = _safe_relpath(src.path) if src.path else ""
+    if path.lower().endswith("skill.md"):
+        files[path] = _fetch_text(_raw_url(src, path))
+        parent = "/".join(path.split("/")[:-1])
+        if parent:
+            try:
+                _list_github_dir(src, parent, files)
+            except SkillImportError:
+                pass
+        return files, src
+
+    if path:
+        try:
+            _fetch_text(_raw_url(src, f"{path}/SKILL.md"))
+            _list_github_dir(src, path, files)
+            return files, src
+        except Exception:
+            pass
+        try:
+            text = _fetch_text(_raw_url(src, path))
+            if path.lower().endswith(".md"):
+                files[path] = text
+                return files, src
+        except Exception:
+            pass
+        _list_github_dir(src, path, files)
+    else:
+        _list_github_dir(src, "", files)
+
+    if not any(p.lower().endswith("skill.md") for p in files):
+        # Flat repo root with SKILL.md only
+        try:
+            files["SKILL.md"] = _fetch_text(_raw_url(src, "SKILL.md"))
+        except Exception as e:
+            raise SkillImportError(
+                "No SKILL.md found — link to a skill folder or SKILL.md on GitHub"
+            ) from e
+    return files, src
+
+
+def pick_skill_md(files: Dict[str, str]) -> Tuple[str, str]:
+    for rel, content in files.items():
+        if rel.lower().endswith("skill.md"):
+            return rel, content
+    raise SkillImportError("bundle has no SKILL.md")
+
+
+def default_category_from_source(src: ResolvedSource) -> str:
+    return "imported"
@@ -381,6 +381,54 @@ class SkillsManager:

        return sk.to_dict()

+    def import_bundle_from_files(
+        self,
+        files: Dict[str, str],
+        *,
+        owner: Optional[str] = None,
+        source_url: str = "",
+        category: str = "imported",
+    ) -> Dict:
+        """Install a fetched skill bundle (relative path → text) under skills/."""
+        from .skill_importer import SkillImportError, pick_skill_md, _safe_relpath
+        from core.atomic_io import atomic_write_text
+
+        if not files:
+            raise SkillImportError("empty bundle")
+        _rel, skill_md = pick_skill_md(files)
+        sk = Skill.from_markdown(skill_md)
+        nm = slugify(sk.name or _rel.split("/")[-2] or "skill")
+        cat = slugify(category or sk.category or "imported", fallback="imported")
+
+        existing = {s["name"] for s in self.load_all()}
+        base = nm
+        i = 2
+        while nm in existing:
+            nm = f"{base}-{i}"
+            i += 1
+
+        skill_dir = self._skill_dir(cat, nm)
+        os.makedirs(skill_dir, exist_ok=True)
+
+        # Preserve bundle layout (templates/, references/, etc.) under the skill dir.
+        for rel, content in files.items():
+            safe = _safe_relpath(rel)
+            dest = os.path.join(skill_dir, safe)
+            os.makedirs(os.path.dirname(dest), exist_ok=True)
+            atomic_write_text(dest, content)
+
+        sk.name = nm
+        sk.category = cat
+        sk.owner = owner
+        sk.source = "imported"
+        if source_url:
+            extra = (sk.body_extra or "").strip()
+            note = f"Imported from {source_url}"
+            sk.body_extra = f"{extra}\n\n{note}".strip() if extra else note
+        atomic_write_text(self._skill_file(cat, nm), sk.to_markdown())
+        sk.path = self._skill_file(cat, nm)
+        return sk.to_dict()
+
    def update_skill(self, skill_id: str, updates: Dict, owner: Optional[str] = None) -> bool:
        """`skill_id` is the slug name. Allows updating any field plus
        renames if `name` changes (file is moved on disk).
@@ -15,10 +15,11 @@ from pathlib import Path
 from typing import Optional, Dict

 from src.research_utils import is_low_quality
+from src.constants import DEEP_RESEARCH_DIR

 logger = logging.getLogger(__name__)

-RESEARCH_DATA_DIR = Path("data/deep_research")
+RESEARCH_DATA_DIR = Path(DEEP_RESEARCH_DIR)


 class ResearchHandler:
@@ -6,21 +6,29 @@ from collections import Counter
 from pathlib import Path
 from typing import Dict, Any

+from core.constants import DATA_DIR
+
 from .cache import cache_metrics

 logger = logging.getLogger(__name__)

-# Dedicated error logger with file handler
-_error_log_path = Path(__file__).resolve().parent.parent / "search_engine_error.log"
-_error_handler = logging.FileHandler(_error_log_path, encoding="utf-8")
-_error_handler.setLevel(logging.WARNING)
-_error_handler.setFormatter(logging.Formatter("%(asctime)s %(levelname)s %(name)s %(message)s"))
+# Dedicated error logger — write to the data logs directory (writable on both
+# native runs and Docker, where DATA_DIR resolves to the bind-mounted volume).
+_log_dir = Path(DATA_DIR) / "logs"
+_error_log_path = _log_dir / "search_engine_error.log"
 error_logger = logging.getLogger("search_engine_error")
-error_logger.addHandler(_error_handler)
 error_logger.propagate = False
+try:
+    _log_dir.mkdir(parents=True, exist_ok=True)
+    _error_handler = logging.FileHandler(_error_log_path, encoding="utf-8")
+    _error_handler.setLevel(logging.WARNING)
+    _error_handler.setFormatter(logging.Formatter("%(asctime)s %(levelname)s %(name)s %(message)s"))
+    error_logger.addHandler(_error_handler)
+except Exception as _e:
+    logging.getLogger(__name__).warning("search_engine_error log handler unavailable: %s", _e)

-# Analytics file
-ANALYTICS_FILE = Path(__file__).resolve().parent.parent / "search_analytics.json"
+# Analytics file — also in the writable logs volume.
+ANALYTICS_FILE = _log_dir / "search_analytics.json"


 # ----------------------------------------------------------------------
@@ -6,17 +6,23 @@ from datetime import datetime, timedelta
 from pathlib import Path
 from typing import Dict

+from core.constants import DATA_DIR
+
 logger = logging.getLogger(__name__)

 # Cache directories
-CACHE_DIR = Path(__file__).resolve().parent.parent / "cache"
+CACHE_DIR = Path(DATA_DIR) / "cache"
 SEARCH_CACHE_DIR = CACHE_DIR / "search"
 CONTENT_CACHE_DIR = CACHE_DIR / "content"
 CACHE_MAX_ENTRIES = 1000

-# Create cache directories
-SEARCH_CACHE_DIR.mkdir(parents=True, exist_ok=True)
-CONTENT_CACHE_DIR.mkdir(parents=True, exist_ok=True)
+# Create cache directories. Guarded so an unwritable path (e.g. a read-only
+# mount) degrades to no-disk-cache instead of crashing module import.
+try:
+    SEARCH_CACHE_DIR.mkdir(parents=True, exist_ok=True)
+    CONTENT_CACHE_DIR.mkdir(parents=True, exist_ok=True)
+except OSError as _e:
+    logger.warning("Search cache directory unavailable (%s); disk cache disabled", _e)

 # Track cache size for LRU eviction
 search_cache_index: Dict[str, datetime] = {}
@@ -259,6 +259,9 @@ def fetch_webpage_content(url: str, timeout: int = 5, retry_attempt: int = 0) ->
            raise RateLimitError(f"Rate limit hit for {url} (attempt {retry_attempt})")

        response.raise_for_status()
+    except httpx.HTTPStatusError as e:
+        error_logger.warning(f"HTTP {e.response.status_code} fetching {url}: {e}")
+        return _empty_result(url, f"HTTP {e.response.status_code}: {e}")
    except httpx.RequestError as e:
        error_logger.error(f"NetworkError fetching {url} (attempt {retry_attempt}): {e}")
        return _empty_result(url, f"NetworkError: {e}")
@@ -134,9 +134,10 @@ _NEWS_HINTS = ("news", "nyheter", "headlines", "breaking", "latest", "today", "i
 _GENERAL_ENGINES = os.environ.get("SEARXNG_GENERAL_ENGINES", "bing,mojeek,presearch")


-def searxng_search_api(query: str, count: int = 10, categories: str = "general",
+def searxng_search_api(query: str, count: Optional[int] = None, categories: str = "general",
                       time_filter: Optional[str] = None) -> List[dict]:
    """Search using SearXNG JSON API. Returns list of {title, url, snippet}."""
+    count = count if count is not None else _get_result_count()
    instance = _get_search_instance()
    api_key = ""
    headers = {"User-Agent": "Mozilla/5.0"}
@@ -282,8 +283,9 @@ def searxng_search(query, max_results=10):

 # ── Brave ──

-def brave_search(query: str, count: int = 10, time_filter: Optional[str] = None) -> List[dict]:
+def brave_search(query: str, count: Optional[int] = None, time_filter: Optional[str] = None) -> List[dict]:
    """Search using Brave API with key from admin settings or env var."""
+    count = count if count is not None else _get_result_count()
    api_key = _get_provider_key("brave") or os.environ.get("DATA_BRAVE_API_KEY") or ""
    return _brave_search_impl(query, count, time_filter, search_config={"brave_api_key": api_key})

@@ -381,9 +383,9 @@ def _resolve_ddg_redirect(raw: str) -> str:
    return resolved


-def duckduckgo_search(query: str, count: int = 10, time_filter: Optional[str] = None) -> List[dict]:
+def duckduckgo_search(query: str, count: Optional[int] = None, time_filter: Optional[str] = None) -> List[dict]:
    """Search using DuckDuckGo via the duckduckgo-search library. No API key needed."""
-
+    count = count if count is not None else _get_result_count()
    def _html_fallback() -> List[dict]:
        try:
            response = httpx.get(
@@ -452,7 +454,7 @@ def duckduckgo_search(query: str, count: int = 10, time_filter: Optional[str] =

 # ── Google Programmable Search Engine ──

-def google_pse_search(query: str, count: int = 10, time_filter: Optional[str] = None) -> List[dict]:
+def google_pse_search(query: str, count: Optional[int] = None, time_filter: Optional[str] = None) -> List[dict]:
    """Search using Google PSE (Custom Search JSON API).

    Requires two keys in settings:
@@ -460,6 +462,7 @@ def google_pse_search(query: str, count: int = 10, time_filter: Optional[str] =
      - google_pse_cx: Programmable Search Engine ID (cx)
    Or env vars GOOGLE_API_KEY and GOOGLE_PSE_CX.
    """
+    count = count if count is not None else _get_result_count()
    settings = _get_search_settings()
    api_key = _get_provider_key("google_pse") or os.environ.get("GOOGLE_API_KEY", "")
    cx = (settings.get("google_pse_cx") or "").strip() or os.environ.get("GOOGLE_PSE_CX", "")
@@ -522,8 +525,9 @@ def google_pse_search(query: str, count: int = 10, time_filter: Optional[str] =

 # ── Tavily ──

-def tavily_search(query: str, count: int = 10, time_filter: Optional[str] = None) -> List[dict]:
+def tavily_search(query: str, count: Optional[int] = None, time_filter: Optional[str] = None) -> List[dict]:
    """Search using Tavily API. Requires search_api_key or TAVILY_API_KEY env var."""
+    count = count if count is not None else _get_result_count()
    api_key = _get_provider_key("tavily") or os.environ.get("TAVILY_API_KEY", "")
    if not api_key:
        logger.warning("Tavily: no API key configured")
@@ -580,8 +584,9 @@ def tavily_search(query: str, count: int = 10, time_filter: Optional[str] = None

 # ── Serper.dev ──

-def serper_search(query: str, count: int = 10, time_filter: Optional[str] = None) -> List[dict]:
+def serper_search(query: str, count: Optional[int] = None, time_filter: Optional[str] = None) -> List[dict]:
    """Search using Serper.dev API. Requires search_api_key or SERPER_API_KEY env var."""
+    count = count if count is not None else _get_result_count()
    api_key = _get_provider_key("serper") or os.environ.get("SERPER_API_KEY", "")
    if not api_key:
        logger.warning("Serper: no API key configured")
@@ -76,6 +76,19 @@ def _domain(url: str) -> str:
        return ""


+def _has_word(text: str, term: str) -> bool:
+    """True if ``term`` appears in ``text`` as a whole word.
+
+    Query terms are matched on word boundaries so a short term doesn't match
+    inside an unrelated word: "us" must not match "business"/"music", "port"
+    must not match "transport"/"support". This mirrors the tokenization used to
+    build ``query_terms`` (``\\b\\w+\\b``). #1473 converted the title and sports
+    checks to word boundaries; the snippet and subject-term checks below use
+    the same helper so the whole file stays consistent.
+    """
+    return re.search(rf"\b{re.escape(term)}\b", text) is not None
+
+
 def rank_search_results(query: str, results: List[dict]) -> List[dict]:
    """Rank search results by title relevance, snippet quality, domain authority, and recency."""
    query_terms = [t.lower() for t in re.findall(r"\b\w+\b", query)]
@@ -87,14 +100,14 @@ def rank_search_results(query: str, results: List[dict]) -> List[dict]:
        if not title:
            return 0.0
        title_lc = title.lower()
-        matches = sum(1 for term in query_terms if re.search(rf"\b{re.escape(term)}\b", title_lc))
+        matches = sum(1 for term in query_terms if _has_word(title_lc, term))
        return matches / len(query_terms) if query_terms else 0.0

    def snippet_score(snippet: str) -> float:
        if not snippet:
            return 0.0
        length_factor = min(len(snippet), 200) / 200
-        term_hits = sum(1 for term in query_terms if term in snippet.lower())
+        term_hits = sum(1 for term in query_terms if _has_word(snippet.lower(), term))
        term_factor = term_hits / len(query_terms) if query_terms else 0.0
        return (length_factor + term_factor) / 2

@@ -127,7 +140,7 @@ def rank_search_results(query: str, results: List[dict]) -> List[dict]:
        # A country/news query should not rank a page whose title/snippet barely
        # mentions the country above actual news pages for that country.
        subject_terms = [t for t in query_terms if t not in _NEWS_HINTS]
-        if subject_terms and not any(t in text or t in netloc for t in subject_terms):
+        if subject_terms and not any(_has_word(text, t) or _has_word(netloc, t) for t in subject_terms):
            adjustment -= 1.0
        return adjustment

@@ -9,6 +9,8 @@ import httpx
 from pathlib import Path
 from typing import Optional, Dict, Any

+from src.constants import TTS_CACHE_DIR
+
 logger = logging.getLogger(__name__)


@@ -35,7 +37,7 @@ class TTSService:
      "endpoint:<id>"   — OpenAI-compatible /audio/speech via ModelEndpoint
    """

-    def __init__(self, cache_dir: str = "data/tts_cache"):
+    def __init__(self, cache_dir: str = TTS_CACHE_DIR):
        self.cache_dir = Path(cache_dir)
        self.cache_dir.mkdir(parents=True, exist_ok=True)
        self._kokoro = None  # lazy-init
@@ -6,23 +6,30 @@ initial admin user. Safe to re-run (skips what already exists).
 """

 import os
+import platform
 import shutil
+import subprocess
 import sys

 BASE_DIR = os.path.dirname(os.path.abspath(__file__))
-DATA_DIR = os.path.join(BASE_DIR, "data")
+sys.path.insert(0, BASE_DIR)
+from src.constants import (
+    DATA_DIR, AUTH_FILE, UPLOAD_DIR, PERSONAL_DIR, PERSONAL_UPLOADS_DIR,
+    TTS_CACHE_DIR, GENERATED_IMAGES_DIR, DEEP_RESEARCH_DIR, CHROMA_DIR,
+    RAG_DIR, MEMORY_VECTORS_DIR,
+)

 DIRS = [
    DATA_DIR,
-    os.path.join(DATA_DIR, "uploads"),
-    os.path.join(DATA_DIR, "personal_docs"),
-    os.path.join(DATA_DIR, "personal_uploads"),
-    os.path.join(DATA_DIR, "tts_cache"),
-    os.path.join(DATA_DIR, "generated_images"),
-    os.path.join(DATA_DIR, "deep_research"),
-    os.path.join(DATA_DIR, "chroma"),
-    os.path.join(DATA_DIR, "rag"),
-    os.path.join(DATA_DIR, "memory_vectors"),
+    UPLOAD_DIR,
+    PERSONAL_DIR,
+    PERSONAL_UPLOADS_DIR,
+    TTS_CACHE_DIR,
+    GENERATED_IMAGES_DIR,
+    DEEP_RESEARCH_DIR,
+    CHROMA_DIR,
+    RAG_DIR,
+    MEMORY_VECTORS_DIR,
    os.path.join(BASE_DIR, "logs"),
 ]

@@ -72,7 +79,7 @@ def _prompt_admin_credentials():

 def create_default_admin():
    """Create an initial admin user if none exists."""
-    auth_path = os.path.join(DATA_DIR, "auth.json")
+    auth_path = AUTH_FILE
    if os.path.exists(auth_path):
        print("  [skip] auth.json already exists")
        return "exists"
@@ -117,7 +124,16 @@ def create_default_admin():
                print(f"        Temporary password: {password}")
                print(f"        ** Change it after first login. Set ODYSSEUS_ADMIN_PASSWORD to choose your own. **")
        return "created"
-    except ImportError:
+    except ImportError as e:
+        if "incompatible architecture" in str(e).lower():
+            # bcrypt is present but built for the wrong CPU architecture — the
+            # same Apple Silicon mismatch check_arch() guards against, caught here
+            # for the rarer case of an x86 wheel inside an arm64 venv.
+            print("  [error] bcrypt loaded with the wrong CPU architecture.")
+            print("          Rebuild the venv with an arm64 Python:")
+            print("            rm -rf venv && /opt/homebrew/bin/python3.11 -m venv venv")
+            print("            ./venv/bin/pip install -r requirements.txt")
+            return "skipped"
        print("  [warn] bcrypt not installed — skipping admin user creation")
        print("         Run: pip install bcrypt")
        return "skipped"
@@ -167,9 +183,52 @@ def check_deps():
        print("  [ok] tmux installed")


+def check_arch():
+    """Stop early, with guidance, if we're on Apple Silicon but running an
+    Intel (x86_64) Python through Rosetta.
+
+    A venv built with such an interpreter installs and loads compiled packages
+    (bcrypt, pydantic-core, onnxruntime, …) for the wrong CPU architecture, then
+    dies deep inside an import with a cryptic
+    "(mach-o file, but is an incompatible architecture)" error. Catching it here
+    turns that into one clear, actionable message.
+    """
+    if sys.platform != "darwin" or platform.machine() == "arm64":
+        return  # Not macOS, or already an arm64-native interpreter — nothing to do.
+
+    # platform.machine() == "x86_64": either a genuine Intel Mac (fine) or an x86
+    # interpreter running under Rosetta on Apple Silicon (the case we must catch).
+    try:
+        translated = subprocess.run(
+            ["sysctl", "-n", "sysctl.proc_translated"],
+            capture_output=True, text=True, timeout=5,
+        ).stdout.strip()
+    except Exception:
+        translated = ""
+    if translated != "1":
+        return  # Genuine Intel Mac — carry on.
+
+    print("\n  [error] This is an Apple Silicon Mac, but setup is running under an")
+    print("          Intel (x86_64) Python through Rosetta. Compiled packages would")
+    print('          load as the wrong architecture and crash with "incompatible')
+    print('          architecture" later on.')
+    print("\n          Rebuild the environment with Homebrew's arm64 Python:")
+    print("            brew install python@3.11          # if you don't have it yet")
+    print("            rm -rf venv")
+    print("            /opt/homebrew/bin/python3.11 -m venv venv")
+    print("            ./venv/bin/pip install -r requirements.txt")
+    print("            ./venv/bin/python setup.py")
+    print("\n          Tip: ./start-macos.sh does all of this with the right Python.\n")
+    sys.exit(1)
+
+
 def main():
    print("\n=== Odysseus Setup ===\n")

+    # Fail fast with a clear message if the CPU architecture is wrong (Apple
+    # Silicon under an x86/Rosetta Python) before importing anything native.
+    check_arch()
+
    print("1. Creating directories...")
    create_dirs()

@@ -35,6 +35,7 @@ _CALENDAR_ACTION = (
    r"delete|deleting|remove|removing|cancel|cancelling|canceling)"
 )
 _CALENDAR_THING = r"(?:calendar|calendar\s+(?:entry|item)|event|meeting|appointment|entry|call)"
+_CALENDAR_READ_THING = r"(?:calendar|schedule|events?|meetings?|appointments?|classes?)"
 _EXPLANATORY_PREFIX = re.compile(
    r"^\s*(?:how\s+(?:do|can)\s+i|can\s+you\s+explain|what\s+about|tell\s+me\s+how|show\s+me\s+how)\b",
    re.I,
@@ -59,6 +60,14 @@ _ROUTING_PATTERNS: tuple[tuple[str, str, Pattern[str]], ...] = tuple(
        ("calendar", "calendar target action request", rf"\b{_CALENDAR_ACTION}\b.{{0,120}}\b(?:to|on|in|into|for)\s+(?:my\s+|the\s+|this\s+)?calendar\b"),
        ("calendar", "put item on calendar request", r"\bput\s+.+\bon\s+(?:my\s+)?calendar\b"),

+        # Calendar/event lookup. A question such as "Do I have Taekwondo
+        # classes this week?" needs the calendar tool; plain chat cannot know.
+        ("calendar", "calendar lookup request", rf"\b(?:list|show|check|find)\b.{{0,120}}\b(?:my\s+|the\s+)?(?:upcoming|next|today'?s?|tomorrow'?s?|this\s+week'?s?)\b.{{0,120}}\b{_CALENDAR_READ_THING}\b"),
+        ("calendar", "calendar lookup question", rf"\b(?:what|which)\b.{{0,120}}\b(?:upcoming|next|today'?s?|tomorrow'?s?|this\s+week'?s?)\b.{{0,120}}\b{_CALENDAR_READ_THING}\b"),
+        ("calendar", "calendar availability question", rf"\bdo\s+i\s+have\b.{{0,120}}\b(?:upcoming|next|today|tomorrow|this\s+week)\b.{{0,120}}\b{_CALENDAR_READ_THING}\b"),
+        ("calendar", "calendar agenda question", r"\bwhat(?:'s| is)\s+on\s+(?:my\s+)?calendar\b"),
+        ("calendar", "next calendar item question", r"\bwhen\s+(?:is|are)\s+(?:my\s+)?next\s+(?:event|meeting|appointment|class)\b"),
+
        # Notes, todos, checklists, and reminders.
        ("notes", "reminder request", r"\bremind\s+me\b"),
        ("notes", "assistant note/todo action request", rf"{_ACTION_QUESTION}(?:add|create|make|take|jot|write\s+down|set)\b.{{0,120}}\b(?:note|todo|task|checklist|reminder)\b"),
@@ -14,16 +14,17 @@ Sub-modules:
 import logging
 from collections import namedtuple

+from src.tool_utils import _truncate, get_mcp_manager, set_mcp_manager
+
 logger = logging.getLogger(__name__)

 # ---------------------------------------------------------------------------
-# Constants (kept here — sub-modules import from here)
+# Constants (re-exported for backward compatibility — single source of truth
+# is src.constants; always prefer importing from there for new code)
 # ---------------------------------------------------------------------------
-MAX_AGENT_ROUNDS = 20
+MAX_AGENT_ROUNDS = 50
 SHELL_TIMEOUT = 60
 PYTHON_TIMEOUT = 30
-MAX_OUTPUT_CHARS = 10_000
-MAX_READ_CHARS = 20_000

 # Tool types that trigger execution
 TOOL_TAGS = {"bash", "python", "web_search", "web_fetch", "read_file", "write_file", "edit_file",
@@ -34,7 +35,7 @@ TOOL_TAGS = {"bash", "python", "web_search", "web_fetch", "read_file", "write_fi
             "send_to_session",
             "pipeline",
             "manage_session", "manage_memory", "list_models",
-             "ui_control", "generate_image",
+             "ui_control", "generate_image", "ask_user", "update_plan",
             "manage_tasks", "api_call", "ask_teacher", "manage_skills",
             "suggest_document",
             "manage_endpoints", "manage_mcp", "manage_webhooks",
@@ -63,33 +64,6 @@ TOOL_TAGS = {"bash", "python", "web_search", "web_fetch", "read_file", "write_fi

 ToolBlock = namedtuple("ToolBlock", ["tool_type", "content"])

-# ---------------------------------------------------------------------------
-# MCP Manager (kept here — used by execution and agent_loop)
-# ---------------------------------------------------------------------------
-_mcp_manager = None
-
-def set_mcp_manager(manager):
-    """Set the global MCP manager instance."""
-    global _mcp_manager
-    _mcp_manager = manager
-
-def get_mcp_manager():
-    """Get the global MCP manager instance."""
-    return _mcp_manager
-
-# ---------------------------------------------------------------------------
-# Helpers (kept here — used by sub-modules)
-# ---------------------------------------------------------------------------
-def _truncate(text: str, limit: int = MAX_OUTPUT_CHARS) -> str:
-    # Callers treat the result as text, so always return a string: coerce a
-    # non-string (None -> "", otherwise str(...)) instead of returning it raw,
-    # which would just move the crash downstream.
-    if not isinstance(text, str):
-        text = "" if text is None else str(text)
-    if len(text) > limit:
-        return text[:limit] + f"\n... (truncated, {len(text)} chars total)"
-    return text
-
 # ---------------------------------------------------------------------------
 # Re-exports from sub-modules
 # ---------------------------------------------------------------------------
@@ -14,6 +14,8 @@ import uuid
 import time
 from typing import Dict, Optional, Tuple

+from src.constants import GENERATED_IMAGES_DIR
+
 logger = logging.getLogger(__name__)

 AI_CHAT_TIMEOUT = 120  # seconds for a single LLM call
@@ -55,7 +57,7 @@ def set_rag_manager(rag_mgr, personal_docs_mgr=None):
 # Model resolution
 # ---------------------------------------------------------------------------

-from src.endpoint_resolver import normalize_base as _normalize_base, build_chat_url, build_headers, build_models_url
+from src.endpoint_resolver import build_chat_url, build_headers, build_models_url, resolve_endpoint_runtime


 def _resolve_model(spec: str, owner: Optional[str] = None) -> Tuple[str, str, Dict]:
@@ -96,9 +98,12 @@ def _resolve_model(spec: str, owner: Optional[str] = None) -> Tuple[str, str, Di
                             (f" matching '{target_endpoint_name}'" if target_endpoint_name else ""))

        for ep in endpoints:
-            base = _normalize_base(ep.base_url)
+            try:
+                base, api_key = resolve_endpoint_runtime(ep, owner=owner)
+            except Exception:
+                continue
            provider = _detect_provider(base)
-            headers = build_headers(ep.api_key, base)
+            headers = build_headers(api_key, base)

            if provider == "anthropic":
                # Anthropic: match against hardcoded model list
@@ -112,16 +117,20 @@ def _resolve_model(spec: str, owner: Optional[str] = None) -> Tuple[str, str, Di
            else:
                # OpenAI-compatible and native Ollama: probe the provider's model list.
                try:
-                    r = httpx.get(build_models_url(base), headers=headers, timeout=5)
-                    r.raise_for_status()
-                    data = r.json()
-                    model_ids = [m.get("id") for m in (data.get("data") or []) if m.get("id")]
-                    if not model_ids:
-                        model_ids = [
-                            m.get("name") or m.get("model")
-                            for m in (data.get("models") or [])
-                            if m.get("name") or m.get("model")
-                        ]
+                    models_url = build_models_url(base)
+                    if models_url:
+                        r = httpx.get(models_url, headers=headers, timeout=5)
+                        r.raise_for_status()
+                        data = r.json()
+                        model_ids = [m.get("id") for m in (data.get("data") or []) if m.get("id")]
+                        if not model_ids:
+                            model_ids = [
+                                m.get("name") or m.get("model")
+                                for m in (data.get("models") or [])
+                                if m.get("name") or m.get("model")
+                            ]
+                    else:
+                        model_ids = json.loads(ep.cached_models or "[]")
                except Exception:
                    model_ids = []

@@ -1119,25 +1128,32 @@ async def do_list_models(content: str, session_id: Optional[str] = None, owner:
        total_models = 0

        for ep in endpoints:
-            base = _normalize_base(ep.base_url)
+            try:
+                base, api_key = resolve_endpoint_runtime(ep, owner=owner)
+            except Exception:
+                continue
            provider = _detect_provider(base)
-            headers = build_headers(ep.api_key, base)
+            headers = build_headers(api_key, base)

            model_ids = []
            if provider == "anthropic":
                model_ids = list(ANTHROPIC_MODELS)
            else:
                try:
-                    r = httpx.get(build_models_url(base), headers=headers, timeout=5)
-                    r.raise_for_status()
-                    data = r.json()
-                    model_ids = [m.get("id") for m in (data.get("data") or []) if m.get("id")]
-                    if not model_ids:
-                        model_ids = [
-                            m.get("name") or m.get("model")
-                            for m in (data.get("models") or [])
-                            if m.get("name") or m.get("model")
-                        ]
+                    models_url = build_models_url(base)
+                    if models_url:
+                        r = httpx.get(models_url, headers=headers, timeout=5)
+                        r.raise_for_status()
+                        data = r.json()
+                        model_ids = [m.get("id") for m in (data.get("data") or []) if m.get("id")]
+                        if not model_ids:
+                            model_ids = [
+                                m.get("name") or m.get("model")
+                                for m in (data.get("models") or [])
+                                if m.get("name") or m.get("model")
+                            ]
+                    else:
+                        model_ids = json.loads(ep.cached_models or "[]")
                except Exception:
                    model_ids = ["(endpoint offline)"]

@@ -1268,7 +1284,7 @@ async def do_ui_control(content: str, session_id: Optional[str] = None, owner: O
      toggle <name> <on|off>  — Toggle a setting (web, bash, rag, research, incognito, document_editor)
      set_mode <agent|chat>   — Switch between agent and chat mode
      switch_model <model>    — Change the model for the current session
-      set_theme <preset>      — Apply a theme preset (dark, light, paper, nord, dracula, gruvbox, gpt, claude, lavender, etc.)
+      set_theme <preset>      — Apply a built-in theme preset (dark, light, midnight, paper, cyberpunk, retrowave, forest, ocean, ume, copper, terminal, organs, lavender, gpt, claude, cute)
      create_theme <name> <bg> <fg> <panel> <border> <accent> [key=val ...] — Create custom theme. Optional key=val: advanced color overrides AND background effects: bgPattern=<none|dots|synapse|rain|constellations|perlin-flow|petals|sparkles|embers>, bgEffectColor=#RRGGBB, bgEffectIntensity=<num>, bgEffectSize=<num>, frosted=true|false
      open_panel <name>       — Open a panel (documents, gallery, email, sessions, notes, memories, skills, settings, cookbook)
      open_email_reply <uid> [folder] [reply|reply-all|ai-reply] — Open a reply draft document for an email; does not send
@@ -1715,7 +1731,7 @@ async def do_generate_image(content: str, session_id: Optional[str] = None, owne

            # GPT image models always return b64_json; DALL-E may return url
            if img.get("b64_json"):
-                img_dir = Path("data/generated_images")
+                img_dir = Path(GENERATED_IMAGES_DIR)
                img_dir.mkdir(parents=True, exist_ok=True)
                filename = f"{uuid.uuid4().hex[:12]}.png"
                img_path = img_dir / filename
@@ -1728,7 +1744,7 @@ async def do_generate_image(content: str, session_id: Optional[str] = None, owne
                try:
                    dl_resp = httpx.get(img["url"], timeout=60)
                    if dl_resp.status_code == 200:
-                        img_dir = Path("data/generated_images")
+                        img_dir = Path(GENERATED_IMAGES_DIR)
                        img_dir.mkdir(parents=True, exist_ok=True)
                        filename = f"{uuid.uuid4().hex[:12]}.png"
                        img_path = img_dir / filename
@@ -10,7 +10,7 @@ def get_current_user(request: Request) -> Optional[str]:
    return getattr(request.state, 'current_user', None)


-def effective_user(request: Request):
+def effective_user(request: Request) -> Optional[str]:
    """The real human behind the request, for ownership/attribution.

    Cookie sessions resolve to the logged-in username. Bearer ``ody_`` callers
@@ -34,6 +34,24 @@ def effective_user(request: Request):
    return get_current_user(request)


+def _is_api_token_request(request: Request) -> bool:
+    """Return True when middleware authenticated a bearer API token."""
+    return bool(getattr(request.state, "api_token", False))
+
+
+def require_authenticated_request(request: Request) -> str:
+    """Allow either a browser session or a valid bearer API token.
+
+    This is intentionally narrower than :func:`require_user`: use it only for
+    routes that need authentication but do not read or mutate owner-scoped
+    user data. Owner-scoped routes should use ``require_user`` for browser
+    sessions or their own API-token scope/owner gate.
+    """
+    if _is_api_token_request(request):
+        return effective_user(request) or ""
+    return require_user(request)
+
+
 def _auth_disabled() -> bool:
    """True when the operator has explicitly turned off auth via .env.
    Mirrors the AUTH_ENABLED parse in app.py / core/middleware.py so the
@@ -60,6 +78,9 @@ def require_user(request: Request) -> str:
    Use this on routes that touch user data so middleware misconfig can't
    open them up.
    """
+    if _is_api_token_request(request):
+        raise HTTPException(403, "API tokens must use a scope-aware API route")
+
    u = get_current_user(request)
    if u:
        return u
@@ -33,13 +33,15 @@ from core.atomic_io import atomic_write_json
 from core.platform_compat import (
    detached_popen_kwargs,
    find_bash,
+    git_bash_path,
    kill_process_tree,
    pid_alive,
 )

-_DATA_DIR = Path(os.environ.get("DATA_DIR", "data"))
-_JOBS_DIR = _DATA_DIR / "bg_jobs"
-_STORE = _DATA_DIR / "bg_jobs.json"
+from src.constants import BG_JOBS_DIR, BG_JOBS_FILE
+
+_JOBS_DIR = Path(BG_JOBS_DIR)
+_STORE = Path(BG_JOBS_FILE)

 # A job that runs longer than this is presumed stuck and reaped (the agent
 # still gets a "timed out" follow-up so nothing hangs forever).
@@ -106,7 +108,7 @@ def launch(command: str, session_id: str, cwd: Optional[str] = None,
        # handles drive paths and spaces correctly.
        cmd_path = _JOBS_DIR / f"{job_id}.cmd.sh"
        cmd_path.write_text(command + "\n", encoding="utf-8")
-        lp, xp, cp = (shlex.quote(p.as_posix()) for p in (log_path, exit_path, cmd_path))
+        lp, xp, cp = (shlex.quote(git_bash_path(p)) for p in (log_path, exit_path, cmd_path))
        script_path = _JOBS_DIR / f"{job_id}.sh"
        script_path.write_text(
            f"bash {cp} > {lp} 2>&1\n"
--- a/Show More
+++ b/Show More