Merge pull request #473 from cbcoutinho/fix/multi-user-basicauth-app-password-storage

fix(auth): Store app passwords locally for multi-user BasicAuth background sync

nextcloud_mcp_server/alembic/versions/20260113_1200_002_add_app_passwords.py

@@ -0,0 +1,50 @@
+"""Add app_passwords table for multi-user BasicAuth mode
+
+This migration adds support for storing app passwords that are provisioned
+via Astrolabe's personal settings. This enables background sync in
+multi-user BasicAuth mode without requiring OAuth.
+
+Revision ID: 002
+Revises: 001
+Create Date: 2026-01-13 12:00:00.000000
+
+"""
+
+from alembic import op
+
+# revision identifiers, used by Alembic.
+revision = "002"
+down_revision = "001"
+branch_labels = None
+depends_on = None
+
+
+def upgrade() -> None:
+    """Add app_passwords table for multi-user BasicAuth mode."""
+
+    # App passwords table for multi-user BasicAuth background sync
+    op.execute(
+        """
+        CREATE TABLE IF NOT EXISTS app_passwords (
+            user_id TEXT PRIMARY KEY,
+            encrypted_password BLOB NOT NULL,
+            created_at INTEGER NOT NULL,
+            updated_at INTEGER NOT NULL
+        )
+        """
+    )
+
+    # Index for efficient user lookups
+    op.execute(
+        """
+        CREATE INDEX IF NOT EXISTS idx_app_passwords_updated
+        ON app_passwords(updated_at)
+        """
+    )
+
+
+def downgrade() -> None:
+    """Drop app_passwords table."""
+
+    op.execute("DROP INDEX IF EXISTS idx_app_passwords_updated")
+    op.execute("DROP TABLE IF EXISTS app_passwords")

nextcloud_mcp_server/api/management.py

@@ -10,12 +10,18 @@ All endpoints use OAuth bearer token authentication via UnifiedTokenVerifier.
 The PHP app obtains tokens through PKCE flow and uses them to access these endpoints.
 """
 
+import base64
 import logging
+import re
 import time
+from collections import defaultdict
 from importlib.metadata import version
-from typing import Any
+from typing import TYPE_CHECKING, Any
 
 import httpx
+
+if TYPE_CHECKING:
+    from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
 from starlette.requests import Request
 from starlette.responses import JSONResponse
 
@@ -25,6 +31,23 @@ logger = logging.getLogger(__name__)
 # Get package version from metadata
 __version__ = version("nextcloud-mcp-server")
 
+# App password format regex (Nextcloud format: xxxxx-xxxxx-xxxxx-xxxxx-xxxxx)
+APP_PASSWORD_PATTERN = re.compile(
+    r"^[a-zA-Z0-9]{5}-[a-zA-Z0-9]{5}-[a-zA-Z0-9]{5}-[a-zA-Z0-9]{5}-[a-zA-Z0-9]{5}$"
+)
+
+# Timeout for Nextcloud API validation requests (seconds)
+NEXTCLOUD_VALIDATION_TIMEOUT = 10.0
+
+# Rate limiting configuration for app password provisioning
+# Limits: 5 attempts per user per hour
+RATE_LIMIT_MAX_ATTEMPTS = 5
+RATE_LIMIT_WINDOW_SECONDS = 3600  # 1 hour
+
+# In-memory rate limiter storage
+# Structure: {user_id: [(timestamp, success), ...]}
+_rate_limit_attempts: dict[str, list[tuple[float, bool]]] = defaultdict(list)
+
 # Track server start time for uptime calculation
 _server_start_time = time.time()
 
@@ -181,6 +204,141 @@ def _validate_query_string(query: str, max_length: int = 10000) -> None:
         raise ValueError(f"Query too long: maximum {max_length} characters")
 
 
+async def _get_app_password_storage(request: Request) -> "RefreshTokenStorage":
+    """Get or initialize RefreshTokenStorage for app password operations.
+
+    Checks app.state.storage first, then falls back to creating from environment.
+    This helper avoids repeated storage initialization logic across endpoints.
+
+    Args:
+        request: Starlette request with app state
+
+    Returns:
+        Initialized RefreshTokenStorage instance
+    """
+    from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
+
+    storage = getattr(request.app.state, "storage", None)
+
+    if not storage:
+        # Multi-user BasicAuth mode may not have oauth_context
+        # Initialize storage from environment
+        storage = RefreshTokenStorage.from_env()
+        await storage.initialize()
+
+    return storage
+
+
+def _check_rate_limit(user_id: str) -> tuple[bool, int]:
+    """Check if user is rate limited for app password operations.
+
+    Implements a sliding window rate limiter to prevent brute-force attacks
+    on the app password provisioning endpoint.
+
+    Args:
+        user_id: User identifier to check
+
+    Returns:
+        Tuple of (is_allowed, seconds_until_retry)
+        - is_allowed: True if request should be allowed
+        - seconds_until_retry: Seconds to wait if rate limited (0 if allowed)
+    """
+    current_time = time.time()
+    window_start = current_time - RATE_LIMIT_WINDOW_SECONDS
+
+    # Clean up old attempts outside the window
+    _rate_limit_attempts[user_id] = [
+        (ts, success)
+        for ts, success in _rate_limit_attempts[user_id]
+        if ts > window_start
+    ]
+
+    # Count recent attempts (both successful and failed)
+    recent_attempts = len(_rate_limit_attempts[user_id])
+
+    if recent_attempts >= RATE_LIMIT_MAX_ATTEMPTS:
+        # Find when the oldest attempt in the window will expire
+        oldest_attempt = min(ts for ts, _ in _rate_limit_attempts[user_id])
+        seconds_until_retry = int(
+            oldest_attempt + RATE_LIMIT_WINDOW_SECONDS - current_time
+        )
+        return False, max(1, seconds_until_retry)
+
+    return True, 0
+
+
+def _record_rate_limit_attempt(user_id: str, success: bool) -> None:
+    """Record an app password provisioning attempt for rate limiting.
+
+    Args:
+        user_id: User identifier
+        success: Whether the attempt was successful
+    """
+    _rate_limit_attempts[user_id].append((time.time(), success))
+
+
+def _extract_basic_auth(
+    request: Request, path_user_id: str
+) -> tuple[str, str, JSONResponse | None]:
+    """Extract and validate BasicAuth credentials from request.
+
+    Validates:
+    1. Authorization header is present and valid BasicAuth format
+    2. Username in credentials matches the path user_id
+
+    Args:
+        request: Starlette request with Authorization header
+        path_user_id: User ID from the URL path to verify against
+
+    Returns:
+        Tuple of (username, password, error_response)
+        - If successful: (username, password, None)
+        - If failed: ("", "", JSONResponse with error)
+    """
+    auth_header = request.headers.get("Authorization")
+
+    if not auth_header or not auth_header.startswith("Basic "):
+        return (
+            "",
+            "",
+            JSONResponse(
+                {"success": False, "error": "Missing BasicAuth credentials"},
+                status_code=401,
+            ),
+        )
+
+    try:
+        # Decode BasicAuth
+        encoded = auth_header.split(" ", 1)[1]
+        decoded = base64.b64decode(encoded).decode("utf-8")
+        username, password = decoded.split(":", 1)
+    except Exception:
+        return (
+            "",
+            "",
+            JSONResponse(
+                {"success": False, "error": "Invalid BasicAuth format"},
+                status_code=401,
+            ),
+        )
+
+    # Verify username matches path user_id
+    if username != path_user_id:
+        logger.warning(
+            f"Username mismatch in app password operation for path user {path_user_id}"
+        )
+        return (
+            "",
+            "",
+            JSONResponse(
+                {"success": False, "error": "Username does not match path user_id"},
+                status_code=403,
+            ),
+        )
+
+    return username, password, None
+
+
 async def get_server_status(request: Request) -> JSONResponse:
     """GET /api/v1/status - Server status and version.
 
@@ -510,6 +668,254 @@ async def revoke_user_access(request: Request) -> JSONResponse:
         )
 
 
+async def provision_app_password(request: Request) -> JSONResponse:
+    """POST /api/v1/users/{user_id}/app-password - Store app password for background sync.
+
+    This endpoint is used by Astrolabe (Nextcloud PHP app) to provision app passwords
+    for multi-user BasicAuth mode background sync.
+
+    The request must include BasicAuth credentials where:
+    - username: Nextcloud user ID (must match path user_id)
+    - password: The app password being provisioned
+
+    The MCP server validates the app password against Nextcloud before storing it.
+    This proves the user owns the password and has access to Nextcloud.
+
+    Security model:
+    - User identity is verified via BasicAuth against Nextcloud
+    - App password is encrypted before storage
+    - Only the user who owns the password can provision it
+    - Rate limited to prevent brute-force attacks
+    """
+    from nextcloud_mcp_server.config import get_settings
+
+    # Get user_id from path
+    path_user_id = request.path_params.get("user_id")
+    if not path_user_id:
+        return JSONResponse(
+            {"success": False, "error": "Missing user_id in path"},
+            status_code=400,
+        )
+
+    # Check rate limit before processing
+    is_allowed, retry_after = _check_rate_limit(path_user_id)
+    if not is_allowed:
+        logger.warning(
+            f"Rate limit exceeded for app password provisioning: {path_user_id}"
+        )
+        return JSONResponse(
+            {
+                "success": False,
+                "error": f"Rate limit exceeded. Try again in {retry_after} seconds.",
+            },
+            status_code=429,
+            headers={"Retry-After": str(retry_after)},
+        )
+
+    # Extract and validate BasicAuth credentials
+    username, app_password, error_response = _extract_basic_auth(request, path_user_id)
+    if error_response is not None:
+        _record_rate_limit_attempt(path_user_id, success=False)
+        return error_response
+
+    # Validate app password format
+    if not APP_PASSWORD_PATTERN.match(app_password):
+        _record_rate_limit_attempt(path_user_id, success=False)
+        return JSONResponse(
+            {"success": False, "error": "Invalid app password format"},
+            status_code=400,
+        )
+
+    # Get Nextcloud host from settings
+    settings = get_settings()
+    nextcloud_host = settings.nextcloud_host
+
+    if not nextcloud_host:
+        logger.error("NEXTCLOUD_HOST not configured")
+        return JSONResponse(
+            {"success": False, "error": "Server not configured"},
+            status_code=500,
+        )
+
+    # Validate app password against Nextcloud
+    try:
+        async with httpx.AsyncClient(timeout=NEXTCLOUD_VALIDATION_TIMEOUT) as client:
+            # Use OCS API to verify credentials
+            test_url = f"{nextcloud_host}/ocs/v1.php/cloud/user"
+            response = await client.get(
+                test_url,
+                auth=(username, app_password),
+                params={"format": "json"},
+                headers={"OCS-APIRequest": "true"},
+            )
+
+            if response.status_code != 200:
+                logger.warning(
+                    f"App password validation failed for user: HTTP {response.status_code}"
+                )
+                _record_rate_limit_attempt(path_user_id, success=False)
+                return JSONResponse(
+                    {"success": False, "error": "Invalid app password"},
+                    status_code=401,
+                )
+
+            # Verify the user ID from response matches
+            data = response.json()
+            ocs_user_id = data.get("ocs", {}).get("data", {}).get("id")
+            if ocs_user_id != username:
+                logger.warning("User ID mismatch in OCS response")
+                _record_rate_limit_attempt(path_user_id, success=False)
+                return JSONResponse(
+                    {"success": False, "error": "User ID mismatch"},
+                    status_code=403,
+                )
+
+    except httpx.RequestError as e:
+        logger.error(f"Failed to validate app password: {e}")
+        return JSONResponse(
+            {"success": False, "error": "Failed to validate credentials"},
+            status_code=500,
+        )
+
+    # Store the validated app password
+    try:
+        storage = await _get_app_password_storage(request)
+        await storage.store_app_password(username, app_password)
+
+        _record_rate_limit_attempt(path_user_id, success=True)
+        logger.info(f"Provisioned app password for user: {username}")
+
+        return JSONResponse(
+            {
+                "success": True,
+                "message": f"App password stored for {username}",
+            }
+        )
+
+    except Exception as e:
+        error_msg = _sanitize_error_for_client(e, "provision_app_password")
+        return JSONResponse(
+            {"success": False, "error": error_msg},
+            status_code=500,
+        )
+
+
+async def get_app_password_status(request: Request) -> JSONResponse:
+    """GET /api/v1/users/{user_id}/app-password - Check if user has provisioned app password.
+
+    Returns status of background sync access for multi-user BasicAuth mode.
+
+    Requires BasicAuth with the user's app password for authentication.
+    """
+    # Get user_id from path
+    path_user_id = request.path_params.get("user_id")
+    if not path_user_id:
+        return JSONResponse(
+            {"success": False, "error": "Missing user_id in path"},
+            status_code=400,
+        )
+
+    # Extract and validate BasicAuth credentials
+    username, _, error_response = _extract_basic_auth(request, path_user_id)
+    if error_response is not None:
+        return error_response
+
+    try:
+        storage = await _get_app_password_storage(request)
+        app_password = await storage.get_app_password(username)
+
+        return JSONResponse(
+            {
+                "success": True,
+                "user_id": username,
+                "has_app_password": app_password is not None,
+            }
+        )
+
+    except Exception as e:
+        error_msg = _sanitize_error_for_client(e, "get_app_password_status")
+        return JSONResponse(
+            {"success": False, "error": error_msg},
+            status_code=500,
+        )
+
+
+async def delete_app_password(request: Request) -> JSONResponse:
+    """DELETE /api/v1/users/{user_id}/app-password - Delete stored app password.
+
+    Removes the user's app password from MCP server storage.
+
+    Requires BasicAuth with the user's credentials.
+    """
+    from nextcloud_mcp_server.config import get_settings
+
+    # Get user_id from path
+    path_user_id = request.path_params.get("user_id")
+    if not path_user_id:
+        return JSONResponse(
+            {"success": False, "error": "Missing user_id in path"},
+            status_code=400,
+        )
+
+    # Extract and validate BasicAuth credentials
+    username, password, error_response = _extract_basic_auth(request, path_user_id)
+    if error_response is not None:
+        return error_response
+
+    # Validate credentials against Nextcloud
+    settings = get_settings()
+    nextcloud_host = settings.nextcloud_host
+
+    try:
+        async with httpx.AsyncClient(timeout=NEXTCLOUD_VALIDATION_TIMEOUT) as client:
+            test_url = f"{nextcloud_host}/ocs/v1.php/cloud/user"
+            response = await client.get(
+                test_url,
+                auth=(username, password),
+                params={"format": "json"},
+                headers={"OCS-APIRequest": "true"},
+            )
+
+            if response.status_code != 200:
+                return JSONResponse(
+                    {"success": False, "error": "Invalid credentials"},
+                    status_code=401,
+                )
+    except httpx.RequestError as e:
+        logger.error(f"Failed to validate credentials: {e}")
+        return JSONResponse(
+            {"success": False, "error": "Failed to validate credentials"},
+            status_code=500,
+        )
+
+    try:
+        storage = await _get_app_password_storage(request)
+        deleted = await storage.delete_app_password(username)
+
+        if deleted:
+            logger.info(f"Deleted app password for user: {username}")
+            return JSONResponse(
+                {
+                    "success": True,
+                    "message": f"App password deleted for {username}",
+                }
+            )
+        else:
+            return JSONResponse(
+                {
+                    "success": True,
+                    "message": "No app password found to delete",
+                }
+            )
+
+    except Exception as e:
+        error_msg = _sanitize_error_for_client(e, "delete_app_password")
+        return JSONResponse(
+            {"success": False, "error": error_msg},
+            status_code=500,
+        )
+
+
 async def get_installed_apps(request: Request) -> JSONResponse:
     """GET /api/v1/apps - Get list of installed Nextcloud apps.
 

nextcloud_mcp_server/app.py

@@ -2012,7 +2012,7 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
             checks["auth_mode"] = "multi_user_basic"
             checks["auth_configured"] = "ok"
             # Indicate if app passwords are supported (when offline_access enabled)
-            checks["supports_app_passwords"] = settings.enable_offline_access
+            checks["supports_app_passwords"] = get_settings().enable_offline_access
         elif mode == AuthMode.SINGLE_USER_BASIC:
             username = os.getenv("NEXTCLOUD_USERNAME")
             password = os.getenv("NEXTCLOUD_PASSWORD")
@@ -2029,9 +2029,9 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
 
         # Check Qdrant status if using network mode (external Qdrant service)
         # In-memory and persistent modes use embedded Qdrant, no external service to check
-        vector_sync_enabled = (
-            os.getenv("VECTOR_SYNC_ENABLED", "false").lower() == "true"
-        )
+        # Note: get_settings() supports both ENABLE_SEMANTIC_SEARCH and VECTOR_SYNC_ENABLED
+        settings = get_settings()
+        vector_sync_enabled = settings.vector_sync_enabled
         qdrant_url = os.getenv("QDRANT_URL")  # Only set in network mode
 
         if vector_sync_enabled and qdrant_url:
@@ -2114,13 +2114,16 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
     if enable_management_apis:
         from nextcloud_mcp_server.api.management import (
             create_webhook,
+            delete_app_password,
             delete_webhook,
+            get_app_password_status,
             get_chunk_context,
             get_installed_apps,
             get_server_status,
             get_user_session,
             get_vector_sync_status,
             list_webhooks,
+            provision_app_password,
             revoke_user_access,
             unified_search,
             vector_search,
@@ -2148,6 +2151,28 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
                 methods=["POST"],
             )
         )
+        # App password endpoints for multi-user BasicAuth mode
+        routes.append(
+            Route(
+                "/api/v1/users/{user_id}/app-password",
+                provision_app_password,
+                methods=["POST"],
+            )
+        )
+        routes.append(
+            Route(
+                "/api/v1/users/{user_id}/app-password",
+                get_app_password_status,
+                methods=["GET"],
+            )
+        )
+        routes.append(
+            Route(
+                "/api/v1/users/{user_id}/app-password",
+                delete_app_password,
+                methods=["DELETE"],
+            )
+        )
         routes.append(
             Route("/api/v1/vector-viz/search", vector_search, methods=["POST"])
         )
@@ -2166,6 +2191,7 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
         logger.info(
             "Management API endpoints enabled: /api/v1/status, /api/v1/vector-sync/status, "
             "/api/v1/users/{user_id}/session, /api/v1/users/{user_id}/revoke, "
+            "/api/v1/users/{user_id}/app-password, "
             "/api/v1/vector-viz/search, /api/v1/search, /api/v1/apps, "
             "/api/v1/webhooks"
         )

nextcloud_mcp_server/auth/storage.py

@@ -1240,6 +1240,180 @@ class RefreshTokenStorage:
 
         return deleted
 
+    # ============================================================================
+    # App Password Storage (multi-user BasicAuth mode)
+    # ============================================================================
+
+    async def store_app_password(
+        self,
+        user_id: str,
+        app_password: str,
+    ) -> None:
+        """
+        Store encrypted app password for background sync (multi-user BasicAuth mode).
+
+        Args:
+            user_id: Nextcloud user ID
+            app_password: Nextcloud app password to store
+        """
+        if not self._initialized:
+            await self.initialize()
+
+        if not self.cipher:
+            raise RuntimeError(
+                "Encryption key not configured. "
+                "Set TOKEN_ENCRYPTION_KEY for app password storage."
+            )
+
+        encrypted_password = self.cipher.encrypt(app_password.encode())
+        now = int(time.time())
+
+        start_time = time.time()
+        try:
+            async with aiosqlite.connect(self.db_path) as db:
+                await db.execute(
+                    """
+                    INSERT OR REPLACE INTO app_passwords
+                    (user_id, encrypted_password, created_at, updated_at)
+                    VALUES (
+                        ?,
+                        ?,
+                        COALESCE((SELECT created_at FROM app_passwords WHERE user_id = ?), ?),
+                        ?
+                    )
+                    """,
+                    (user_id, encrypted_password, user_id, now, now),
+                )
+                await db.commit()
+
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "insert", duration, "success")
+            logger.info(f"Stored app password for user {user_id}")
+
+        except Exception:
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "insert", duration, "error")
+            raise
+
+        # Audit log
+        await self._audit_log(
+            event="store_app_password",
+            user_id=user_id,
+            auth_method="app_password",
+        )
+
+    async def get_app_password(self, user_id: str) -> Optional[str]:
+        """
+        Retrieve and decrypt app password for a user.
+
+        Args:
+            user_id: Nextcloud user ID
+
+        Returns:
+            Decrypted app password, or None if not found
+        """
+        if not self._initialized:
+            await self.initialize()
+
+        if not self.cipher:
+            raise RuntimeError(
+                "Encryption key not configured. "
+                "Set TOKEN_ENCRYPTION_KEY for app password retrieval."
+            )
+
+        start_time = time.time()
+        try:
+            async with aiosqlite.connect(self.db_path) as db:
+                async with db.execute(
+                    "SELECT encrypted_password FROM app_passwords WHERE user_id = ?",
+                    (user_id,),
+                ) as cursor:
+                    row = await cursor.fetchone()
+
+            if not row:
+                logger.debug(f"No app password found for user {user_id}")
+                duration = time.time() - start_time
+                record_db_operation("sqlite", "select", duration, "success")
+                return None
+
+            encrypted_password = row[0]
+            decrypted_password = self.cipher.decrypt(encrypted_password).decode()
+
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "select", duration, "success")
+            logger.debug(f"Retrieved app password for user {user_id}")
+
+            return decrypted_password
+
+        except Exception as e:
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "select", duration, "error")
+            logger.error(f"Failed to decrypt app password for user {user_id}: {e}")
+            return None
+
+    async def delete_app_password(self, user_id: str) -> bool:
+        """
+        Delete app password for a user.
+
+        Args:
+            user_id: Nextcloud user ID
+
+        Returns:
+            True if password was deleted, False if not found
+        """
+        if not self._initialized:
+            await self.initialize()
+
+        start_time = time.time()
+        try:
+            async with aiosqlite.connect(self.db_path) as db:
+                cursor = await db.execute(
+                    "DELETE FROM app_passwords WHERE user_id = ?",
+                    (user_id,),
+                )
+                await db.commit()
+                deleted = cursor.rowcount > 0
+
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "delete", duration, "success")
+
+            if deleted:
+                logger.info(f"Deleted app password for user {user_id}")
+                await self._audit_log(
+                    event="delete_app_password",
+                    user_id=user_id,
+                    auth_method="app_password",
+                )
+            else:
+                logger.debug(f"No app password to delete for user {user_id}")
+
+            return deleted
+
+        except Exception:
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "delete", duration, "error")
+            raise
+
+    async def get_all_app_password_user_ids(self) -> list[str]:
+        """
+        Get list of all user IDs with stored app passwords.
+
+        Returns:
+            List of user IDs
+        """
+        if not self._initialized:
+            await self.initialize()
+
+        async with aiosqlite.connect(self.db_path) as db:
+            async with db.execute(
+                "SELECT user_id FROM app_passwords ORDER BY updated_at DESC"
+            ) as cursor:
+                rows = await cursor.fetchall()
+
+        user_ids = [row[0] for row in rows]
+        logger.debug(f"Found {len(user_ids)} users with app passwords")
+        return user_ids
+
 
 async def generate_encryption_key() -> str:
     """

nextcloud_mcp_server/auth/userinfo_routes.py

@@ -20,6 +20,7 @@ from starlette.requests import Request
 from starlette.responses import HTMLResponse, JSONResponse
 
 from nextcloud_mcp_server.client import NextcloudClient
+from nextcloud_mcp_server.config import get_settings
 
 logger = logging.getLogger(__name__)
 
@@ -106,9 +107,9 @@ async def _get_processing_status(request: Request) -> dict[str, Any] | None:
             "status": str,  # "syncing" or "idle"
         }
     """
-    # Check if vector sync is enabled
-    vector_sync_enabled = os.getenv("VECTOR_SYNC_ENABLED", "false").lower() == "true"
-    if not vector_sync_enabled:
+    # Check if vector sync is enabled (supports both old and new env var names)
+    settings = get_settings()
+    if not settings.vector_sync_enabled:
         return None
 
     try:
@@ -127,10 +128,8 @@ async def _get_processing_status(request: Request) -> dict[str, Any] | None:
         # Get Qdrant client and query indexed count
         indexed_count = 0
         try:
-            from nextcloud_mcp_server.config import get_settings
             from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client
 
-            settings = get_settings()
             qdrant_client = await get_qdrant_client()
 
             # Count documents in collection
@@ -634,7 +633,9 @@ async def user_info_html(request: Request) -> HTMLResponse:
         """
 
     # Check if vector sync is enabled (needed for Welcome tab)
-    vector_sync_enabled = os.getenv("VECTOR_SYNC_ENABLED", "false").lower() == "true"
+    # Note: get_settings() supports both ENABLE_SEMANTIC_SEARCH and VECTOR_SYNC_ENABLED
+    settings = get_settings()
+    vector_sync_enabled = settings.vector_sync_enabled
 
     # Render template
     template = _jinja_env.get_template("user_info.html")

nextcloud_mcp_server/server/deck.py

@@ -637,7 +637,9 @@ def configure_deck_tools(mcp: FastMCP):
 
     @mcp.tool(
         title="Remove Label from Deck Card",
-        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+        annotations=ToolAnnotations(
+            destructiveHint=True, idempotentHint=True, openWorldHint=True
+        ),
     )
     @require_scopes("deck:write")
     @instrument_tool
@@ -692,7 +694,9 @@ def configure_deck_tools(mcp: FastMCP):
 
     @mcp.tool(
         title="Unassign User from Deck Card",
-        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+        annotations=ToolAnnotations(
+            destructiveHint=True, idempotentHint=True, openWorldHint=True
+        ),
     )
     @require_scopes("deck:write")
     @instrument_tool

nextcloud_mcp_server/server/semantic.py

@@ -1,7 +1,6 @@
 """Semantic search MCP tools using vector database."""
 
 import logging
-import os
 
 import anyio
 from httpx import RequestError
@@ -658,12 +657,11 @@ def configure_semantic_tools(mcp: FastMCP):
         after creating or updating content across all indexed apps.
         """
 
-        # Check if vector sync is enabled
-        vector_sync_enabled = (
-            os.getenv("VECTOR_SYNC_ENABLED", "false").lower() == "true"
-        )
+        # Check if vector sync is enabled (supports both old and new env var names)
+        from nextcloud_mcp_server.config import get_settings
 
-        if not vector_sync_enabled:
+        settings = get_settings()
+        if not settings.vector_sync_enabled:
             return VectorSyncStatusResponse(
                 indexed_count=0,
                 pending_count=0,

nextcloud_mcp_server/vector/oauth_sync.py

@@ -8,8 +8,8 @@ Manages background vector sync for multi-user deployments:
 Authentication strategies are mutually exclusive by deployment mode:
 
 Multi-user BasicAuth mode (ENABLE_MULTI_USER_BASIC_AUTH=true):
-- Uses app passwords obtained via Astrolabe Management API
-- Users provision via Astrolabe personal settings
+- Uses app passwords stored locally in MCP server's database
+- Users provision via Astrolabe personal settings, which sends to MCP API
 - OAuth is NOT used
 
 OAuth mode (with external IdP like Keycloak):
@@ -33,7 +33,6 @@ from anyio.streams.memory import (
 )
 from httpx import BasicAuth
 
-from nextcloud_mcp_server.auth.astrolabe_client import AstrolabeClient
 from nextcloud_mcp_server.client import NextcloudClient
 from nextcloud_mcp_server.config import get_settings
 from nextcloud_mcp_server.vector.scanner import DocumentTask, scan_user_documents
@@ -71,15 +70,18 @@ class UserSyncState:
 async def get_user_client_basic_auth(
     user_id: str,
     nextcloud_host: str,
+    storage: "RefreshTokenStorage | None" = None,
 ) -> NextcloudClient:
     """Get an authenticated NextcloudClient using app password (BasicAuth mode).
 
     For multi-user BasicAuth deployments where users provision app passwords
-    via Astrolabe personal settings. OAuth is NOT used in this mode.
+    via Astrolabe personal settings. The app password is stored locally in the
+    MCP server's database after being provisioned through the management API.
 
     Args:
         user_id: User identifier
         nextcloud_host: Nextcloud base URL
+        storage: Optional RefreshTokenStorage instance (created from env if not provided)
 
     Returns:
         Authenticated NextcloudClient with BasicAuth
@@ -87,21 +89,15 @@ async def get_user_client_basic_auth(
     Raises:
         NotProvisionedError: If user has not provisioned an app password
     """
-    settings = get_settings()
+    from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
 
-    if not settings.oidc_client_id or not settings.oidc_client_secret:
-        raise NotProvisionedError(
-            "Astrolabe client credentials not configured. "
-            "Set OIDC_CLIENT_ID and OIDC_CLIENT_SECRET for app password retrieval."
-        )
+    # Get or create storage instance
+    if storage is None:
+        storage = RefreshTokenStorage.from_env()
+        await storage.initialize()
 
-    astrolabe = AstrolabeClient(
-        nextcloud_host=nextcloud_host,
-        client_id=settings.oidc_client_id,
-        client_secret=settings.oidc_client_secret,
-    )
-
-    app_password = await astrolabe.get_user_app_password(user_id)
+    # Retrieve app password from local storage
+    app_password = await storage.get_app_password(user_id)
 
     if not app_password:
         raise NotProvisionedError(
@@ -419,8 +415,15 @@ async def user_manager_task(
 
     while not shutdown_event.is_set():
         try:
-            # Get current provisioned users
-            provisioned_users = set(await refresh_token_storage.get_all_user_ids())
+            # Get current provisioned users based on mode
+            if use_basic_auth:
+                # BasicAuth mode: query app_passwords table
+                provisioned_users = set(
+                    await refresh_token_storage.get_all_app_password_user_ids()
+                )
+            else:
+                # OAuth mode: query refresh_tokens table
+                provisioned_users = set(await refresh_token_storage.get_all_user_ids())
             active_users = set(user_states.keys())
 
             # Start scanners for new users