Enforce owner checks for upload attachments

routes/document_helpers.py

@@ -3,6 +3,8 @@
 """Document routes — CRUD for living documents with version history."""
 
 import logging
+import os
+import re
 from typing import Dict, Any, Optional
 
 from fastapi import HTTPException
@@ -12,6 +14,7 @@ from core.database import Document, DocumentVersion
 from core.database import Session as DbSession
 
 logger = logging.getLogger(__name__)
+_UPLOAD_ID_RE = re.compile(r"^[0-9a-fA-F]{32}\.[A-Za-z0-9]+$")
 
 
 # ---- Request schemas ----
@@ -126,40 +129,86 @@ def _slug(name: str) -> str:
 _PDF_RENDER_SCALE = 2.0
 
 
-def _locate_upload(upload_dir: str, file_id: str):
+def _upload_path_inside(upload_dir: str, path: str) -> bool:
+    base = os.path.realpath(upload_dir)
+    p = os.path.realpath(path)
+    try:
+        return os.path.commonpath([base, p]) == base
+    except Exception:
+        return False
+
+
+def _upload_owner_allowed(
+    meta: Optional[dict],
+    user: Optional[str],
+    auth_manager=None,
+    allow_admin: bool = True,
+) -> bool:
+    if not user:
+        return (
+            not bool(auth_manager and getattr(auth_manager, "is_configured", False))
+            and not (meta and meta.get("owner") is not None)
+        )
+    if allow_admin and auth_manager and hasattr(auth_manager, "is_admin"):
+        try:
+            if auth_manager.is_admin(user):
+                return True
+        except Exception:
+            pass
+    return bool(meta and meta.get("owner") == user)
+
+
+def _locate_upload(upload_dir: str, file_id: str, owner: Optional[str] = None, auth_manager=None):
     """Find an upload by its filename ID.
 
     Lookup order:
-      1. Direct hit at `upload_dir/file_id` (very small deployments).
+      1. The `uploads.json` index that `UploadHandler.save_upload` maintains,
-      2. The `uploads.json` index that `UploadHandler.save_upload` maintains —
+         so owner can be verified before a document reads the source file.
-         maps file_hash → metadata containing the full path. O(1) once loaded.
+      2. Direct hit at `upload_dir/file_id` (very small deployments).
       3. Fallback: `os.walk` the date-bucketed tree. Slow on large stores;
-         only triggers for legacy uploads recorded before the index existed.
+         only allowed after the index owner check passes, or in single-user /
+         admin-style contexts where no owner is enforced.
 
     `followlinks=False` keeps a stray symlink loop in `data/uploads/` from
     spinning the walker into infinite recursion.
     """
-    import os
     import json as _json
-    direct = os.path.join(upload_dir, file_id)
+
-    if os.path.exists(direct):
+    if not _UPLOAD_ID_RE.fullmatch(file_id or ""):
-        return direct
+        logger.warning("Rejected invalid upload id in document lookup: %r", file_id)
-    # O(1) via uploads.json
+        return None
+
+    meta = None
     try:
         idx_path = os.path.join(upload_dir, "uploads.json")
         if os.path.exists(idx_path):
             with open(idx_path, "r", encoding="utf-8") as f:
                 idx = _json.load(f)
-            for meta in (idx.values() if isinstance(idx, dict) else []):
+            for item in (idx.values() if isinstance(idx, dict) else []):
-                if meta.get("id") == file_id:
+                if isinstance(item, dict) and item.get("id") == file_id:
-                    p = meta.get("path")
+                    meta = item
-                    if p and os.path.exists(p):
+                    break
-                        return p
     except Exception:
-        pass
+        meta = None
+
+    if not _upload_owner_allowed(meta, owner, auth_manager):
+        logger.warning("Upload %s denied for document owner %s", file_id, owner)
+        return None
+
+    if meta:
+        p = meta.get("path")
+        if p and os.path.exists(p) and _upload_path_inside(upload_dir, p):
+            return p
+
+    direct = os.path.join(upload_dir, file_id)
+    if os.path.exists(direct) and _upload_path_inside(upload_dir, direct):
+        return direct
+
     for root, _dirs, files in os.walk(upload_dir, followlinks=False):
         if file_id in files:
-            return os.path.join(root, file_id)
+            p = os.path.join(root, file_id)
+            if _upload_path_inside(upload_dir, p):
+                return p
     return None
 
 

routes/document_routes.py

@@ -24,6 +24,12 @@ from routes.document_helpers import (
     _PDF_RENDER_SCALE,
 )
 
+
+def _locate_current_user_upload(request: Request, upload_dir: str, upload_id: str, user: Optional[str]):
+    auth_manager = getattr(getattr(request.app, "state", None), "auth_manager", None)
+    return _locate_upload(upload_dir, upload_id, owner=user, auth_manager=auth_manager)
+
+
 def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
     router = APIRouter(tags=["documents"])
 
@@ -160,7 +166,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
             raise HTTPException(500, f"Upload failed: {e}")
 
         upload_id = meta["id"]
-        pdf_path = _locate_upload(UPLOAD_DIR, upload_id)
+        pdf_path = _locate_current_user_upload(request, UPLOAD_DIR, upload_id, user)
         if not pdf_path:
             raise HTTPException(500, "Saved PDF could not be located")
 
@@ -401,7 +407,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
                 raise HTTPException(400, "Document is not a PDF — no pdf_source marker found")
             upload_id = m.group(1)
 
-            pdf_path = _locate_upload(UPLOAD_DIR, upload_id)
+            pdf_path = _locate_current_user_upload(request, UPLOAD_DIR, upload_id, user)
             if not pdf_path:
                 raise HTTPException(404, "Source PDF could not be located")
 
@@ -914,7 +920,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
             if not upload_id:
                 raise HTTPException(400, "Document is not linked to a source PDF")
 
-            pdf_path = _locate_upload(UPLOAD_DIR, upload_id)
+            pdf_path = _locate_current_user_upload(request, UPLOAD_DIR, upload_id, user)
             if not pdf_path:
                 raise HTTPException(404, f"Source PDF {upload_id} not found in uploads")
 
@@ -978,7 +984,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
             upload_id = find_source_upload_id(doc.current_content or "")
             if not upload_id:
                 raise HTTPException(400, "Document is not linked to a source PDF")
-            pdf_path = _locate_upload(UPLOAD_DIR, upload_id)
+            pdf_path = _locate_current_user_upload(request, UPLOAD_DIR, upload_id, user)
             if not pdf_path:
                 raise HTTPException(404, f"Source PDF {upload_id} not found")
 
@@ -1046,7 +1052,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
             upload_id = find_source_upload_id(doc.current_content or "")
             if not upload_id:
                 raise HTTPException(400, "Document is not linked to a source PDF")
-            pdf_path = _locate_upload(UPLOAD_DIR, upload_id)
+            pdf_path = _locate_current_user_upload(request, UPLOAD_DIR, upload_id, user)
             if not pdf_path:
                 raise HTTPException(404, "Source PDF not found")
         finally:
@@ -1101,7 +1107,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
             upload_id = find_source_upload_id(doc.current_content or "")
             if not upload_id:
                 raise HTTPException(400, "Document is not linked to a source PDF")
-            pdf_path = _locate_upload(UPLOAD_DIR, upload_id)
+            pdf_path = _locate_current_user_upload(request, UPLOAD_DIR, upload_id, user)
             if not pdf_path:
                 raise HTTPException(404, "Source PDF not found")
         finally:
@@ -1250,7 +1256,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
             upload_id = find_source_upload_id(doc.current_content or "")
             if not upload_id:
                 raise HTTPException(400, "Document is not linked to a source PDF")
-            pdf_path = _locate_upload(UPLOAD_DIR, upload_id)
+            pdf_path = _locate_current_user_upload(request, UPLOAD_DIR, upload_id, user)
             if not pdf_path:
                 raise HTTPException(404, f"Source PDF {upload_id} not found")
 
@@ -1345,7 +1351,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
             if not upload_id:
                 raise HTTPException(400, "Document is not linked to a source PDF")
 
-            pdf_path = _locate_upload(UPLOAD_DIR, upload_id)
+            pdf_path = _locate_current_user_upload(request, UPLOAD_DIR, upload_id, user)
             if not pdf_path:
                 raise HTTPException(404, f"Source PDF {upload_id} not found in uploads")
 
@@ -1489,7 +1495,7 @@ def setup_document_routes(session_manager, upload_handler=None) -> APIRouter:
             upload_id = find_source_upload_id(doc.current_content or "")
             if not upload_id:
                 raise HTTPException(400, "Document is not linked to a source PDF")
-            pdf_path = _locate_upload(UPLOAD_DIR, upload_id)
+            pdf_path = _locate_current_user_upload(request, UPLOAD_DIR, upload_id, user)
             if not pdf_path:
                 raise HTTPException(404, f"Source PDF {upload_id} not found")
 

src/chat_handler.py

@@ -1,7 +1,6 @@
 # src/chat_handler.py
 """Handler for chat endpoint operations."""
 import os
-import json
 import asyncio
 import logging
 from typing import Dict, List, Optional, Any
@@ -149,23 +148,22 @@ class ChatHandler:
         vision_enabled = get_setting("vision_enabled", True)
         main_is_vision = is_vision_model(sess.model or "")
 
-        # Read uploads DB once and index by id (was read twice + linear-scanned per attachment)
+        # Resolve uploads once with the session owner. Attachment IDs are
+        # bearer-like references; never trust them without an owner check.
         files_by_id: Dict[str, Dict] = {}
+        owner = getattr(sess, "owner", None)
         if att_ids:
-            uploads_db_path = os.path.join(UPLOAD_DIR, "uploads.json")
+            for att_id in att_ids:
-            try:
+                fi = self.upload_handler.resolve_upload(att_id, owner=owner)
-                with open(uploads_db_path, "r", encoding="utf-8") as f:
+                if fi:
-                    _all_files = json.load(f)
+                    files_by_id[att_id] = fi
-                files_by_id = {fi["id"]: fi for fi in _all_files.values() if "id" in fi}
-            except (FileNotFoundError, json.JSONDecodeError):
-                pass
 
             for att_id in att_ids:
                 fi = files_by_id.get(att_id)
                 if fi:
                     attachment_meta.append({
                         "id": fi["id"],
-                        "name": fi["name"],
+                        "name": fi.get("name") or fi.get("original_name") or fi["id"],
                         "mime": fi.get("mime", ""),
                         "size": fi.get("size", 0),
                         "width": fi.get("width"),
@@ -242,6 +240,8 @@ class ChatHandler:
             enhanced_message, att_ids, UPLOAD_DIR, self.upload_handler,
             session_id=getattr(sess, "id", None),
             auto_opened_docs=auto_opened_docs,
+            owner=owner,
+            resolved_uploads=files_by_id,
         )
 
         # Strip image_url entries for text-only models (VL description is already in the text)

src/document_processor.py

@@ -257,6 +257,8 @@ def build_user_content(
     upload_handler,
     session_id: str | None = None,
     auto_opened_docs: list[Dict[str, Any]] | None = None,
+    owner: str | None = None,
+    resolved_uploads: dict[str, Dict[str, Any]] | None = None,
 ) -> str | List[Dict[str, Any]]:
     """Build user content with attachments (text, images, audio, documents).
 
@@ -268,33 +270,30 @@ def build_user_content(
     """
     content = [{"type": "text", "text": text}]
 
-    for fid in attachment_ids:
+    for fid in attachment_ids or []:
-        if not upload_handler.validate_upload_id(fid):
+        upload_info = (resolved_uploads or {}).get(fid)
-            logger.warning(f"Invalid attachment ID format: {fid}")
+        if upload_info is None and hasattr(upload_handler, "resolve_upload"):
+            upload_info = upload_handler.resolve_upload(fid, owner=owner)
+        if upload_info is None:
+            logger.warning(f"Attachment {fid} not found or not authorized")
             continue
 
-        path = os.path.join(upload_dir, fid)
+        path = upload_info.get("path")
-        if not (upload_handler.inside_base_dir(path) and os.path.exists(path)):
+        if not path or not os.path.exists(path):
-            found = False
+            logger.warning(f"Attachment {fid} path is missing")
-            for root, dirs, files in os.walk(upload_dir):
+            continue
-                if fid in files and not fid.endswith(".json"):
+        if hasattr(upload_handler, "_inside_upload_dir") and not upload_handler._inside_upload_dir(path):
-                    path = os.path.join(root, fid)
+            logger.warning(f"Attachment {fid} path is outside upload directory: {path}")
-                    if upload_handler.inside_base_dir(path):
+            continue
-                        found = True
+        if not hasattr(upload_handler, "_inside_upload_dir") and not upload_handler.inside_base_dir(path):
-                        logger.info(f"Found attachment {fid} at {path}")
-                        break
-            if not found:
-                logger.warning(f"Attachment {fid} not found in upload directories")
-                continue
-
-        if not upload_handler.inside_base_dir(path):
             logger.warning(f"Attachment {fid} path is outside base directory: {path}")
             continue
 
         _, ext = os.path.splitext(path.lower())
-        mime = mimetypes.guess_type(path)[0] or "application/octet-stream"
+        mime = upload_info.get("mime") or mimetypes.guess_type(path)[0] or "application/octet-stream"
+        display_name = upload_info.get("name") or upload_info.get("original_name") or path
 
-        if upload_handler.is_image_file(path, mime):
+        if upload_handler.is_image_file(display_name, mime):
             try:
                 with open(path, "rb") as image_file:
                     encoded_string = base64.b64encode(image_file.read()).decode("utf-8")
@@ -310,7 +309,7 @@ def build_user_content(
                 else:
                     content.insert(0, {"type": "text", "text": "[Image attached but could not be processed]"})
 
-        elif upload_handler.is_audio_file(path, mime):
+        elif upload_handler.is_audio_file(display_name, mime):
             try:
                 with open(path, "rb") as audio_file:
                     encoded_string = base64.b64encode(audio_file.read()).decode("utf-8")
@@ -326,7 +325,7 @@ def build_user_content(
                 else:
                     content.insert(0, {"type": "text", "text": "[Audio attached but could not be processed]"})
 
-        elif upload_handler.is_document_file(path, mime):
+        elif upload_handler.is_document_file(display_name, mime):
             if mime == "application/pdf":
                 extracted_text = None
                 if session_id:

src/upload_handler.py

@@ -8,7 +8,7 @@ import hashlib
 import mimetypes
 import threading
 from datetime import datetime, timedelta
-from typing import Dict, Any
+from typing import Dict, Any, Optional
 from fastapi import HTTPException, UploadFile
 def secure_filename(filename: str) -> str:
     """Sanitize a filename (replaces werkzeug.utils.secure_filename)."""
@@ -226,6 +226,106 @@ class UploadHandler:
         pattern = r'^[0-9a-fA-F]{32}\.[A-Za-z0-9]+$'
         return re.fullmatch(pattern, upload_id) is not None
 
+    def _inside_upload_dir(self, path: str) -> bool:
+        """Check if path is inside the upload directory."""
+        base = os.path.realpath(self.upload_dir)
+        p = os.path.realpath(path)
+        try:
+            return os.path.commonpath([base, p]) == base
+        except Exception:
+            return False
+
+    def _load_upload_index(self) -> Dict[str, Any]:
+        uploads_db_path = os.path.join(self.upload_dir, "uploads.json")
+        if not os.path.exists(uploads_db_path):
+            return {}
+        try:
+            with open(uploads_db_path, "r") as f:
+                data = json.load(f)
+            return data if isinstance(data, dict) else {}
+        except Exception as e:
+            logger.warning(f"Failed to read uploads database: {e}")
+            return {}
+
+    def get_upload_info(self, upload_id: str) -> Optional[Dict[str, Any]]:
+        """Return the uploads.json metadata row for an upload ID, if present."""
+        if not self.validate_upload_id(upload_id):
+            return None
+        for info in self._load_upload_index().values():
+            if isinstance(info, dict) and info.get("id") == upload_id:
+                return dict(info)
+        return None
+
+    def _find_upload_path(self, upload_id: str) -> Optional[str]:
+        """Find an upload file by ID while staying inside upload_dir."""
+        if not self.validate_upload_id(upload_id):
+            return None
+
+        direct = os.path.join(self.upload_dir, upload_id)
+        if os.path.exists(direct) and self._inside_upload_dir(direct):
+            return direct
+
+        for root, _dirs, files in os.walk(self.upload_dir, followlinks=False):
+            if upload_id in files:
+                path = os.path.join(root, upload_id)
+                if self._inside_upload_dir(path):
+                    return path
+        return None
+
+    def resolve_upload(
+        self,
+        upload_id: str,
+        owner: Optional[str] = None,
+        auth_manager: Any = None,
+        allow_admin: bool = True,
+    ) -> Optional[Dict[str, Any]]:
+        """Resolve an upload ID to metadata only if the caller may read it.
+
+        This is the owner-aware lookup used by internal processors. Public
+        download routes already perform owner checks; chat/document paths must
+        do the same before reading file bytes server-side.
+        """
+        if not self.validate_upload_id(upload_id):
+            logger.warning(f"Invalid upload ID format: {upload_id}")
+            return None
+
+        auth_configured = bool(auth_manager and getattr(auth_manager, "is_configured", False))
+        if auth_configured and not owner:
+            return None
+
+        info = self.get_upload_info(upload_id) or {}
+        is_admin = False
+        if allow_admin and owner and auth_manager and hasattr(auth_manager, "is_admin"):
+            try:
+                is_admin = bool(auth_manager.is_admin(owner))
+            except Exception:
+                is_admin = False
+
+        if owner and not is_admin:
+            if info.get("owner") != owner:
+                logger.warning("Upload %s denied for owner %s", upload_id, owner)
+                return None
+        if not owner and info.get("owner") is not None:
+            logger.warning("Upload %s denied without an authenticated owner", upload_id)
+            return None
+
+        path = info.get("path")
+        if not path or not os.path.exists(path) or not self._inside_upload_dir(path):
+            path = self._find_upload_path(upload_id)
+        if not path:
+            return None
+        if not self._inside_upload_dir(path):
+            logger.warning(f"Upload path outside upload directory: {path}")
+            return None
+
+        resolved = dict(info)
+        resolved.setdefault("id", upload_id)
+        resolved["path"] = path
+        resolved.setdefault("name", os.path.basename(path))
+        resolved.setdefault("original_name", resolved["name"])
+        resolved.setdefault("mime", mimetypes.guess_type(path)[0] or "application/octet-stream")
+        return resolved
+    
     def cleanup_rate_limits(self):
         """Remove stale entries from upload_rate_log."""
         now = time.time()

tests/test_security_regressions.py

@@ -168,6 +168,145 @@ def test_path_name_strips_traversal(token, expected):
     assert Path(token).name == expected
 
 
+# -- upload owner gates -------------------------------------------------------
+
+def _make_upload_store(tmp_path):
+    upload_dir = tmp_path / "uploads"
+    dated = upload_dir / "2026" / "06" / "01"
+    dated.mkdir(parents=True)
+
+    alice_id = "a" * 32 + ".txt"
+    bob_id = "b" * 32 + ".txt"
+    alice_path = dated / alice_id
+    bob_path = dated / bob_id
+    alice_path.write_text("alice private note", encoding="utf-8")
+    bob_path.write_text("bob private note", encoding="utf-8")
+
+    index = {
+        "alice:h1": {
+            "id": alice_id,
+            "path": str(alice_path),
+            "mime": "text/plain",
+            "size": alice_path.stat().st_size,
+            "name": "alice.txt",
+            "original_name": "alice.txt",
+            "owner": "alice",
+        },
+        "bob:h2": {
+            "id": bob_id,
+            "path": str(bob_path),
+            "mime": "text/plain",
+            "size": bob_path.stat().st_size,
+            "name": "bob.txt",
+            "original_name": "bob.txt",
+            "owner": "bob",
+        },
+    }
+    (upload_dir / "uploads.json").write_text(json.dumps(index), encoding="utf-8")
+    return upload_dir, alice_id, bob_id
+
+
+def _stub_core_database_for_route_imports(monkeypatch):
+    from unittest.mock import MagicMock
+
+    core_pkg = types.ModuleType("core")
+    core_pkg.__path__ = []
+    models = types.ModuleType("core.models")
+    models.ChatMessage = MagicMock()
+
+    db = types.ModuleType("core.database")
+    for name in (
+        "SessionLocal",
+        "Session",
+        "ChatMessage",
+        "Document",
+        "DocumentVersion",
+        "GalleryImage",
+        "ModelEndpoint",
+    ):
+        setattr(db, name, MagicMock())
+    monkeypatch.setitem(sys.modules, "core", core_pkg)
+    monkeypatch.setitem(sys.modules, "core.models", models)
+    monkeypatch.setitem(sys.modules, "core.database", db)
+
+
+def test_upload_resolver_rejects_cross_owner_upload_ids(tmp_path):
+    from src.upload_handler import UploadHandler
+
+    upload_dir, alice_id, bob_id = _make_upload_store(tmp_path)
+    handler = UploadHandler(str(tmp_path), str(upload_dir))
+
+    assert handler.resolve_upload(alice_id, owner="alice")["id"] == alice_id
+    assert handler.resolve_upload(bob_id, owner="alice") is None
+
+
+def test_build_user_content_skips_cross_owner_attachments(tmp_path):
+    from src.document_processor import build_user_content
+    from src.upload_handler import UploadHandler
+
+    upload_dir, _alice_id, bob_id = _make_upload_store(tmp_path)
+    handler = UploadHandler(str(tmp_path), str(upload_dir))
+
+    content = build_user_content(
+        "hello",
+        [bob_id],
+        str(upload_dir),
+        handler,
+        owner="alice",
+    )
+
+    assert content == "hello"
+    assert "bob private note" not in content
+
+
+def test_chat_preprocess_does_not_surface_cross_owner_attachment(tmp_path, monkeypatch):
+    import asyncio
+    from types import SimpleNamespace
+    for mod_name in ("src.chat_handler", "routes.chat_helpers"):
+        sys.modules.pop(mod_name, None)
+    _stub_core_database_for_route_imports(monkeypatch)
+    from src.chat_handler import ChatHandler
+    from src.upload_handler import UploadHandler
+    from src import settings
+
+    upload_dir, _alice_id, bob_id = _make_upload_store(tmp_path)
+    handler = UploadHandler(str(tmp_path), str(upload_dir))
+    monkeypatch.setattr("src.chat_handler.UPLOAD_DIR", str(upload_dir))
+    monkeypatch.setattr(
+        settings,
+        "get_setting",
+        lambda key, default=None: False if key == "vision_enabled" else default,
+    )
+
+    chat_handler = ChatHandler(None, None, None, None, None, handler)
+    sess = SimpleNamespace(id="s1", owner="alice", model="text-model")
+
+    _enhanced, user_content, _text_ctx, _yt, attachment_meta = asyncio.run(
+        chat_handler.preprocess_message(
+            "hello",
+            [bob_id],
+            sess,
+        )
+    )
+
+    assert attachment_meta == []
+    assert user_content == "hello"
+    for mod_name in ("src.chat_handler", "routes.chat_helpers"):
+        sys.modules.pop(mod_name, None)
+
+
+def test_document_upload_lookup_rejects_cross_owner_marker(tmp_path, monkeypatch):
+    sys.modules.pop("routes.document_helpers", None)
+    _stub_core_database_for_route_imports(monkeypatch)
+    from routes.document_helpers import _locate_upload
+
+    upload_dir, _alice_id, bob_id = _make_upload_store(tmp_path)
+
+    assert _locate_upload(str(upload_dir), bob_id, owner="alice") is None
+    assert _locate_upload(str(upload_dir), bob_id, owner="bob").endswith(bob_id)
+    sys.modules.pop("routes.document_helpers", None)
+
+
 # ── require_user dependency rejects anon callers ────────────────
 
 def test_require_user_rejects_unauthenticated(monkeypatch):