chore(deps): bump the python group across 1 directory with 4 updates

Updates the requirements on [httpcore](https://github.com/encode/httpcore), [pydantic-settings](https://github.com/pydantic/pydantic-settings), [mcp](https://github.com/modelcontextprotocol/python-sdk) and [markitdown](https://github.com/microsoft/markitdown) to permit the latest version.

Updates `httpcore` to 1.0.9
- [Release notes](https://github.com/encode/httpcore/releases)
- [Changelog](https://github.com/encode/httpcore/blob/master/CHANGELOG.md)
- [Commits](https://github.com/encode/httpcore/compare/1.0.0...1.0.9)

Updates `pydantic-settings` to 2.14.2
- [Release notes](https://github.com/pydantic/pydantic-settings/releases)
- [Commits](https://github.com/pydantic/pydantic-settings/compare/v2.14.1...v2.14.2)

Updates `mcp` to 2.0.0
- [Release notes](https://github.com/modelcontextprotocol/python-sdk/releases)
- [Changelog](https://github.com/modelcontextprotocol/python-sdk/blob/main/RELEASE.md)
- [Commits](https://github.com/modelcontextprotocol/python-sdk/compare/v0.2.0...v2.0.0)

Updates `markitdown` from 0.1.6 to 0.1.7
- [Release notes](https://github.com/microsoft/markitdown/releases)
- [Commits](https://github.com/microsoft/markitdown/compare/v0.1.6...v0.1.7)

---
updated-dependencies:
- dependency-name: httpcore
  dependency-version: 1.0.9
  dependency-type: direct:production
  dependency-group: python
- dependency-name: pydantic-settings
  dependency-version: 2.14.2
  dependency-type: direct:production
  dependency-group: python
- dependency-name: mcp
  dependency-version: 2.0.0
  dependency-type: direct:production
  dependency-group: python
- dependency-name: markitdown
  dependency-version: 0.1.7
  dependency-type: direct:production
  update-type: version-update:semver-patch
  dependency-group: python
...

Signed-off-by: dependabot[bot] <support@github.com>

requirements-optional.txt

@@ -33,4 +33,4 @@ PyMuPDF
 # magika (onnxruntime), already a core dep via fastembed. We avoid the
 # [all]/Azure/audio extras (cloud + heavy). Pinned to a release >30 days old per
 # the dependency-age discussion in issue #485.
-markitdown[docx,pptx,xlsx,xls]==0.1.6
+markitdown[docx,pptx,xlsx,xls]==0.1.7

requirements.txt

@@ -3,9 +3,9 @@ uvicorn
 python-multipart
 python-dotenv
 httpx
-httpcore>=1.0,<2.0
+httpcore>=1.0.9,<2.0
 pydantic>=2.13.4
-pydantic-settings>=2.14.1
+pydantic-settings>=2.14.2
 SQLAlchemy
 pypdf
 beautifulsoup4
@@ -41,7 +41,7 @@ bcrypt
 # Built-in servers use the v1 low-level Server decorator API. MCP SDK v2 is a
 # breaking rewrite, so keep fresh installs on the maintained v1 line until the
 # servers are migrated together.
-mcp<2
+mcp<3
 pyotp
 qrcode[pil]
 croniter

routes/skills_routes.py

@@ -1409,7 +1409,7 @@ def setup_skills_routes(skills_manager: SkillsManager) -> APIRouter:
 
         # Prefer the configured DEFAULT (→ Utility) model — not the current chat
         # session's model. Fall back to the caller's session model only if unset.
-        url, model, headers = resolve_endpoint("default", owner=user)
+        url, model, headers = resolve_endpoint("utility", owner=user)
         if not url or not model:
             url = url or ((body.get("endpoint_url") or "").strip() or None)
             model = model or ((body.get("model") or "").strip() or None)

services/memory/skill_format.py

@@ -50,7 +50,7 @@ import json
 import logging
 import re
 from dataclasses import dataclass, field
-from datetime import datetime
+from datetime import datetime, timezone
 from typing import Any, Dict, List, Optional
 
 logger = logging.getLogger(__name__)
@@ -441,4 +441,4 @@ class Skill:
 
 
 def _now_iso() -> str:
-    return datetime.utcnow().strftime("%Y-%m-%dT%H:%M:%SZ")
+    return datetime.now(timezone.utc).strftime("%Y-%m-%dT%H:%M:%SZ")

src/llm_core.py

@@ -1237,15 +1237,27 @@ def _anthropic_rejects_temperature(model: str) -> bool:
         return False
     # `(?<![a-z])` anchors "opus" to a word boundary so a substring match like
     # `oct-opus`/`octopus-4-8` can't be read as Opus (it would otherwise strip
-    # temperature). Cap the minor at 1-2 digits and forbid a trailing digit so a
-    # dated id like `claude-opus-4-20250514` (Opus 4.0) parses as major-only (no
-    # minor match, kept) instead of reading the date `20250514` as a giant minor
-    # that would falsely test >= 4.7. Dated 4.7+ snapshots (`claude-opus-4-7-
-    # 20260201`) keep their explicit minor and are still matched.
-    match = re.search(r"(?<![a-z])opus[-_]?(\d+)[-_.](\d{1,2})(?!\d)", model.lower())
+    # temperature). Both version components are capped at 1-2 digits and forbid a
+    # trailing digit, so an 8-digit date can never be read as a version number:
+    # `claude-opus-4-20250514` (Opus 4.0) parses as major-only rather than reading
+    # `20250514` as a giant minor, and `claude-3-opus-20240229` (legacy Claude 3
+    # Opus, date directly after "opus-") fails to match at all rather than reading
+    # the date as a giant major. Dated 4.7+ snapshots (`claude-opus-4-7-20260201`)
+    # keep their explicit minor and are still matched.
+    #
+    # The minor is optional and a missing minor reads as `.0`, so major-only ids
+    # like `claude-opus-5` are correctly treated as >= 4.7 (issue #5753). Without
+    # this, every Opus 5 call kept `temperature` and failed with HTTP 400 — visible
+    # only on paths that pass a temperature, e.g. scheduled tasks inheriting
+    # `stream_agent_loop`'s 0.3 default, which returned empty responses.
+    match = re.search(
+        r"(?<![a-z])opus[-_]?(\d{1,2})(?!\d)(?:[-_.](\d{1,2})(?!\d))?", model.lower()
+    )
     if not match:
         return False
-    return (int(match.group(1)), int(match.group(2))) >= (4, 7)
+    major = int(match.group(1))
+    minor = int(match.group(2)) if match.group(2) else 0
+    return (major, minor) >= (4, 7)
 
 # Reasoning effort level sent to Mistral thinking-capable models. Mistral's
 # API accepts "high", "medium", "low", "none" — see

static/js/markdown.js

@@ -758,30 +758,36 @@ export function mdToHtml(src, opts) {
   // Remove empty paragraphs
   s = s.replace(/<p><\/p>/g, '');
 
+  // Every restore below passes a function replacer rather than the block string
+  // itself. With a string replacement, `String.replace` reads `$&`, `` $` ``,
+  // `$'` and `$$` in the *replacement* as substitution patterns, so a restored
+  // block containing them is corrupted: `$&` re-inserts the placeholder, `` $` ``
+  // and `$'` splice in the surrounding document, and `$$` collapses to `$`. Those
+  // sequences are ordinary content in fenced code (`perl -pe 's/x/$& y/'`,
+  // `echo "$$USD"`). A function replacer inserts its return value verbatim.
+
   // CRITICAL: Restore allowed HTML blocks first
   allowedHtmlBlocks.forEach((block, index) => {
-    s = s.replace(`___ALLOWED_HTML_${index}___`, block);
+    s = s.replace(`___ALLOWED_HTML_${index}___`, () => block);
   });
 
   // Restore math blocks
   mathBlocks.forEach((block, index) => {
-    s = s.replace(`___MATH_BLOCK_${index}___`, block);
+    s = s.replace(`___MATH_BLOCK_${index}___`, () => block);
   });
 
   // Restore mermaid diagram blocks
   mermaidBlocks.forEach((block, index) => {
-    s = s.replace(`___MERMAID_BLOCK_${index}___`, block);
+    s = s.replace(`___MERMAID_BLOCK_${index}___`, () => block);
   });
 
   // CRITICAL: Restore code blocks at the end
   codeBlocks.forEach((block, index) => {
-    s = s.replace(`___CODE_BLOCK_${index}___`, block);
+    s = s.replace(`___CODE_BLOCK_${index}___`, () => block);
   });
 
   // Restore inline code spans last, so placeholders carried inside restored
-  // <a>/allowed-HTML blocks are resolved too. The function replacer keeps the
-  // escaped code literal — e.g. a shell snippet like `echo $1` is not treated
-  // as a regex back-reference.
+  // <a>/allowed-HTML blocks are resolved too.
   inlineCodeBlocks.forEach((block, index) => {
     s = s.replace(`___INLINE_CODE_${index}___`, () => block);
   });

static/js/settings.js

@@ -3031,12 +3031,14 @@ async function initEmailAccountsSettings() {
       const body = {
         name: el('eaf-name').value.trim() || el('eaf-from').value.trim(),
         from_address: el('eaf-from').value.trim(),
+        display_name: el('eaf-display-name').value.trim(),
         imap_host: el('eaf-imap-host').value.trim(),
         imap_port: parseInt(el('eaf-imap-port').value) || 993,
         imap_user: el('eaf-imap-user').value.trim(),
         imap_starttls: el('eaf-imap-starttls').checked,
         smtp_host: el('eaf-smtp-host').value.trim(),
         smtp_port: parseInt(el('eaf-smtp-port').value) || 587,
+        smtp_security: el('eaf-smtp-security').value,
         smtp_user: el('eaf-imap-user').value.trim(),
       };
       if (!body.name) { el('eaf-msg').textContent = 'Enter a Name or Email first'; el('eaf-msg').style.color = 'var(--red)'; return; }
@@ -5788,29 +5790,30 @@ export function close() {
   window.history.replaceState(null, '', clean);
   const success = sp.has('email_oauth_success');
   const errMsg = sp.get('email_oauth_error') || '';
-  // Open settings → integrations after the app has initialised.
-  function _tryOpen() {
-    if (window.settingsModule && typeof window.settingsModule.open === 'function') {
-      window.settingsModule.open('integrations');
-      // Brief toast-style banner.
-      const banner = document.createElement('div');
-      banner.textContent = success
-        ? '✓ Google account connected — email is ready'
-        : `Google OAuth failed: ${errMsg || 'unknown error'}`;
-      Object.assign(banner.style, {
-        position: 'fixed', bottom: '24px', left: '50%', transform: 'translateX(-50%)',
-        background: success ? 'var(--accent, #50fa7b)' : 'var(--red, #ff5555)',
-        color: '#000', padding: '8px 18px', borderRadius: '6px', fontSize: '12px',
-        fontWeight: '600', zIndex: '99999', pointerEvents: 'none',
-        boxShadow: '0 2px 12px rgba(0,0,0,0.3)',
-      });
-      document.body.appendChild(banner);
-      setTimeout(() => banner.remove(), 4000);
-    } else {
-      setTimeout(_tryOpen, 100);
-    }
+  // Open settings → integrations once the document is ready. This module owns
+  // the open() API, so it does not need to wait for a window-level alias.
+  function _showResult() {
+    open('integrations');
+    // Brief toast-style banner.
+    const banner = document.createElement('div');
+    banner.textContent = success
+      ? 'Google account connected — email is ready'
+      : `Google OAuth failed: ${errMsg || 'unknown error'}`;
+    Object.assign(banner.style, {
+      position: 'fixed', bottom: '24px', left: '50%', transform: 'translateX(-50%)',
+      background: success ? 'var(--accent, #50fa7b)' : 'var(--red, #ff5555)',
+      color: '#000', padding: '8px 18px', borderRadius: '6px', fontSize: '12px',
+      fontWeight: '600', zIndex: '99999', pointerEvents: 'none',
+      boxShadow: '0 2px 12px rgba(0,0,0,0.3)',
+    });
+    document.body.appendChild(banner);
+    setTimeout(() => banner.remove(), 4000);
+  }
+  if (document.readyState === 'loading') {
+    document.addEventListener('DOMContentLoaded', _showResult, { once: true });
+  } else {
+    _showResult();
   }
-  _tryOpen();
 })();
 
 const settingsModule = { open, close, initIntegrations, initUnifiedIntegrations, syncAdminVisibility, refreshAiModelEndpoints };

tests/test_email_oauth_connect_smtp_security.py

@@ -0,0 +1,15 @@
+"""Regression coverage for SMTP security saved before Google OAuth."""
+
+from pathlib import Path
+
+
+_REPO = Path(__file__).resolve().parents[1]
+
+
+def test_email_tab_oauth_connect_persists_selected_smtp_security():
+    source = (_REPO / "static" / "js" / "settings.js").read_text(encoding="utf-8")
+    start = source.index("el('eaf-oauth-btn').addEventListener")
+    handler_body = source[start:source.index("if (!body.name)", start)]
+
+    assert "smtp_security: el('eaf-smtp-security').value" in handler_body
+    assert "display_name: el('eaf-display-name').value.trim()" in handler_body

tests/test_email_oauth_settings_redirect.py

@@ -0,0 +1,19 @@
+"""Regression coverage for the settings UI after Google OAuth redirects."""
+
+from pathlib import Path
+
+
+_REPO = Path(__file__).resolve().parents[1]
+
+
+def test_oauth_redirect_uses_the_module_local_settings_api():
+    source = (_REPO / "static" / "js" / "settings.js").read_text(encoding="utf-8")
+    handler = source[
+        source.index("(function _handleOauthRedirect"):
+        source.index("const settingsModule =")
+    ]
+
+    assert "open('integrations');" in handler
+    assert "window.settingsModule" not in handler
+    assert "window.__odysseusAppStarted" not in handler
+    assert "document.addEventListener('DOMContentLoaded', _showResult, { once: true })" in handler

tests/test_llm_core_anthropic_temp_omit.py

@@ -29,6 +29,13 @@ from src.llm_core import _anthropic_rejects_temperature, _build_anthropic_payloa
         "anthropic/claude-opus-4-7",  # tolerate a provider-prefixed id
         "claude-opus-4-10",  # future minor still >= 4.7
         "claude-opus-5-0",  # future major
+        # Major-only ids: a missing minor reads as `.0`, so these are >= 4.7 too
+        # (issue #5753). Before the fix the version pattern required a minor, so
+        # these fell through to "accepts temperature" and every call 400'd.
+        "claude-opus-5",
+        "claude-opus-5-20260101",  # major-only + dated snapshot
+        "anthropic/claude-opus-5",  # major-only behind a provider prefix
+        "claude-opus-6",  # future major-only
     ],
 )
 def test_opus_47_plus_rejects_temperature(model):
@@ -48,7 +55,10 @@ def test_opus_47_plus_rejects_temperature(model):
         "claude-opus-4-6-20251201",  # dated 4.6 snapshot — older, still keeps temperature
         "claude-sonnet-4-6",
         "claude-3-5-sonnet",
-        "claude-3-opus-20240229",  # legacy Claude 3 Opus — no opus-N-M pattern, kept
+        "claude-3-opus-20240229",  # legacy Claude 3 Opus — date directly after
+        # "opus-", so the major must not swallow it as version 20240229 (that is
+        # what makes capping the major at 1-2 digits necessary once the minor
+        # became optional in #5753).
         "claude-haiku-4-5",
         "claude-x",
         "octopus-4-8",  # "opus" only as a substring of another word — must not match
@@ -87,6 +97,20 @@ def test_payload_keeps_temperature_for_older_models():
     assert _payload("claude-3-5-sonnet", 1.2)["temperature"] == 1.0
 
 
+def test_payload_omits_temperature_for_major_only_opus_5():
+    # Issue #5753: the scheduled-task path calls stream_agent_loop() without a
+    # temperature and inherits its 0.3 default, so `claude-opus-5` 400'd on every
+    # run and surfaced as "the model returned an empty response". Interactive chat
+    # leaves temperature None and never hit it.
+    assert "temperature" not in _payload("claude-opus-5", 0.3)
+
+
+def test_payload_keeps_temperature_for_legacy_claude_3_opus():
+    # Guards the major-digit cap: `opus-20240229` must not parse as version
+    # 20240229, or Claude 3 Opus would silently lose the caller's temperature.
+    assert _payload("claude-3-opus-20240229", 0.5)["temperature"] == 0.5
+
+
 def test_payload_keeps_temperature_for_dated_opus_4_0():
     # Anthropic's dated id for Opus 4.0 (claude-opus-4-20250514) is in this repo's
     # ANTHROPIC_MODELS list. The date must not be misread as a >= 4.7 minor, or the

tests/test_markdown_rendering_js.py

@@ -214,6 +214,50 @@ def test_inline_code_content_is_html_escaped(node_available):
     assert "<b>" not in html
 
 
+def test_fenced_code_keeps_dollar_ampersand(node_available):
+    # Issue #5663: the block-restore pass used a string replacement, so `$&` in a
+    # restored block was read as "the matched text" and re-inserted the
+    # placeholder. `perl -pe 's/world/$& again/'` rendered as
+    # "s/world/___CODE_BLOCK_0___amp; again/" — the trailing "amp;" is the orphan
+    # left behind after `$&` consumed the `$&` of the escaped `$&amp;`.
+    html = _run_markdown_case(
+        "```sh\necho \"hello world\" | perl -pe 's/world/$& again/'\n```"
+    )
+
+    assert "___CODE_BLOCK_" not in html
+    assert "s/world/$&amp; again/" in html
+    assert "amp; again" not in html.replace("$&amp; again", "")
+
+
+def test_fenced_code_keeps_dollar_backtick_and_quote(node_available):
+    # `` $` `` and `$'` splice the text before/after the placeholder into the
+    # block. Unlike `$&` these leave no placeholder behind — the characters just
+    # vanish — so assert the content survives verbatim.
+    html = _run_markdown_case("```sh\nsed \"s/$`/x/\" && sed \"s/$'/y/\"\n```")
+
+    assert "___CODE_BLOCK_" not in html
+    assert "s/$`/x/" in html
+    assert "s/$&#39;/y/" in html
+
+
+def test_fenced_code_keeps_double_dollar(node_available):
+    # `$$` collapsed to a single `$` in the restored block.
+    html = _run_markdown_case('```sh\necho "$$USD and $$"\n```')
+
+    assert "$$USD and $$" in html
+
+
+def test_mermaid_block_keeps_dollar_ampersand(node_available):
+    # The mermaid restore site had the same hazard: a node label containing `$&`
+    # re-inserted the ___MERMAID_BLOCK_n___ placeholder into the diagram source,
+    # which then fails to parse. The math and allowed-HTML sites are fixed the
+    # same way; they need KaTeX/sanitizer conditions this harness doesn't set up.
+    html = _run_markdown_case('```mermaid\ngraph TD; A["$&"] --> B;\n```')
+
+    assert "___MERMAID_BLOCK_" not in html
+    assert "$&amp;" in html
+
+
 def test_currency_dollar_amounts_are_not_rendered_as_math(node_available):
     # "$5 to $10" used to pair the two dollar signs as inline-math delimiters
     # and render "5 to" through KaTeX. Pandoc-style rules now reject it: the

tests/test_skill_format_timestamp.py

@@ -0,0 +1,58 @@
+"""Regression for issue #5697 — skill timestamps must not use ``datetime.utcnow()``.
+
+``_now_iso()`` builds the ``created`` value in skill frontmatter. ``utcnow()``
+returns a *naive* datetime and has been deprecated since Python 3.12, scheduled
+for removal. The replacement must stay timezone-aware while keeping the
+serialized ``YYYY-MM-DDTHH:MM:SSZ`` shape, so skill files written by older
+versions keep parsing.
+
+The UTC check matters on its own: a bare ``datetime.now()`` also produces the
+right shape, but emits local wall time, which would silently backdate or
+postdate skills for every user outside UTC.
+"""
+
+import os
+import re
+import time
+import warnings
+from datetime import datetime, timezone
+
+import pytest
+
+from services.memory.skill_format import _now_iso
+
+_ISO_Z = re.compile(r"^\d{4}-\d{2}-\d{2}T\d{2}:\d{2}:\d{2}Z$")
+
+
+def test_now_iso_keeps_serialized_shape():
+    assert _ISO_Z.match(_now_iso())
+
+
+def test_now_iso_emits_no_deprecation_warning():
+    with warnings.catch_warnings(record=True) as caught:
+        warnings.simplefilter("always")
+        _now_iso()
+    assert not [w for w in caught if issubclass(w.category, DeprecationWarning)]
+
+
+@pytest.mark.skipif(
+    not hasattr(time, "tzset"),
+    reason="time.tzset is unavailable on this platform",
+)
+def test_now_iso_is_utc_not_local_time():
+    """Pin UTC under a non-UTC local timezone, where the two visibly diverge."""
+    original_tz = os.environ.get("TZ")
+    os.environ["TZ"] = "Asia/Amman"  # UTC+3, never UTC
+    time.tzset()
+    try:
+        emitted = datetime.strptime(_now_iso(), "%Y-%m-%dT%H:%M:%SZ").replace(
+            tzinfo=timezone.utc
+        )
+        drift = abs((emitted - datetime.now(timezone.utc)).total_seconds())
+        assert drift < 60, f"timestamp is {drift}s off UTC — local time leaked in"
+    finally:
+        if original_tz is None:
+            os.environ.pop("TZ", None)
+        else:
+            os.environ["TZ"] = original_tz
+        time.tzset()