feat: improve Google Calendar and Gmail connectors with enhanced error handling

- Added user-friendly re-authentication messages for expired or revoked tokens in both Google Calendar and Gmail connectors.
- Updated error handling in indexing tasks to log specific authentication errors and provide clearer feedback to users.
- Enhanced the connector UI to handle indexing failures more effectively, improving overall user experience.

surfsense_backend/app/connectors/google_calendar_connector.py

@@ -142,6 +142,12 @@ class GoogleCalendarConnector:
                     flag_modified(connector, "config")
                     await self._session.commit()
             except Exception as e:
+                error_str = str(e)
+                # Check if this is an invalid_grant error (token expired/revoked)
+                if "invalid_grant" in error_str.lower() or "token has been expired or revoked" in error_str.lower():
+                    raise Exception(
+                        "Google Calendar authentication failed. Please re-authenticate."
+                    ) from e
                 raise Exception(
                     f"Failed to refresh Google OAuth credentials: {e!s}"
                 ) from e
@@ -165,6 +171,10 @@ class GoogleCalendarConnector:
             self.service = build("calendar", "v3", credentials=credentials)
             return self.service
         except Exception as e:
+            error_str = str(e)
+            # If the error already contains a user-friendly re-authentication message, preserve it
+            if "re-authenticate" in error_str.lower() or "expired or been revoked" in error_str.lower() or "authentication failed" in error_str.lower():
+                raise Exception(error_str) from e
             raise Exception(f"Failed to create Google Calendar service: {e!s}") from e
 
     async def get_calendars(self) -> tuple[list[dict[str, Any]], str | None]:
@@ -271,6 +281,10 @@ class GoogleCalendarConnector:
             return events, None
 
         except Exception as e:
+            error_str = str(e)
+            # If the error already contains a user-friendly re-authentication message, preserve it
+            if "re-authenticate" in error_str.lower() or "expired or been revoked" in error_str.lower() or "authentication failed" in error_str.lower():
+                return [], error_str
             return [], f"Error fetching events: {e!s}"
 
     def format_event_to_markdown(self, event: dict[str, Any]) -> str:

surfsense_backend/app/connectors/google_gmail_connector.py

@@ -141,6 +141,12 @@ class GoogleGmailConnector:
                     flag_modified(connector, "config")
                     await self._session.commit()
             except Exception as e:
+                error_str = str(e)
+                # Check if this is an invalid_grant error (token expired/revoked)
+                if "invalid_grant" in error_str.lower() or "token has been expired or revoked" in error_str.lower():
+                    raise Exception(
+                        "Gmail authentication failed. Please re-authenticate."
+                    ) from e
                 raise Exception(
                     f"Failed to refresh Google OAuth credentials: {e!s}"
                 ) from e
@@ -164,6 +170,10 @@ class GoogleGmailConnector:
             self.service = build("gmail", "v1", credentials=credentials)
             return self.service
         except Exception as e:
+            error_str = str(e)
+            # If the error already contains a user-friendly re-authentication message, preserve it
+            if "re-authenticate" in error_str.lower() or "expired or been revoked" in error_str.lower() or "authentication failed" in error_str.lower():
+                raise Exception(error_str) from e
             raise Exception(f"Failed to create Gmail service: {e!s}") from e
 
     async def get_user_profile(self) -> tuple[dict[str, Any], str | None]:
@@ -225,6 +235,10 @@ class GoogleGmailConnector:
             return messages, None
 
         except Exception as e:
+            error_str = str(e)
+            # If the error already contains a user-friendly re-authentication message, preserve it
+            if "re-authenticate" in error_str.lower() or "expired or been revoked" in error_str.lower() or "authentication failed" in error_str.lower():
+                return [], error_str
             return [], f"Error fetching messages list: {e!s}"
 
     async def get_message_details(

surfsense_backend/app/tasks/connector_indexers/google_calendar_indexer.py

@@ -246,13 +246,20 @@ async def index_google_calendar_events(
                     )
                     return 0, None
                 else:
+                    # Check if this is an authentication error that requires re-authentication
+                    error_message = error
+                    error_type = "APIError"
+                    if "re-authenticate" in error.lower() or "expired or been revoked" in error.lower() or "authentication failed" in error.lower():
+                        error_message = "Google Calendar authentication failed. Please re-authenticate."
+                        error_type = "AuthenticationError"
+                    
                     await task_logger.log_task_failure(
                         log_entry,
-                        f"Failed to get Google Calendar events: {error}",
+                        error_message,
-                        "API Error",
+                        error,
-                        {"error_type": "APIError"},
+                        {"error_type": error_type},
                     )
-                    return 0, f"Failed to get Google Calendar events: {error}"
+                    return 0, error_message
 
             logger.info(f"Retrieved {len(events)} events from Google Calendar API")
 

surfsense_backend/app/tasks/connector_indexers/google_gmail_indexer.py

@@ -170,10 +170,20 @@ async def index_google_gmail_messages(
         )
 
         if error:
+            # Check if this is an authentication error that requires re-authentication
+            error_message = error
+            error_type = "APIError"
+            if "re-authenticate" in error.lower() or "expired or been revoked" in error.lower() or "authentication failed" in error.lower():
+                error_message = "Gmail authentication failed. Please re-authenticate."
+                error_type = "AuthenticationError"
+            
             await task_logger.log_task_failure(
-                log_entry, f"Failed to fetch messages: {error}", {}
+                log_entry, 
+                error_message,
+                error,
+                {"error_type": error_type}
             )
-            return 0, f"Failed to fetch Gmail messages: {error}"
+            return 0, error_message
 
         if not messages:
             success_msg = "No Google gmail messages found in the specified date range"

surfsense_web/components/assistant-ui/connector-popup.tsx

@@ -5,12 +5,14 @@ import { Cable, Loader2 } from "lucide-react";
 import { useSearchParams } from "next/navigation";
 import type { FC } from "react";
 import { activeSearchSpaceIdAtom } from "@/atoms/search-spaces/search-space-query.atoms";
+import { currentUserAtom } from "@/atoms/user/user-query.atoms";
 import { TooltipIconButton } from "@/components/assistant-ui/tooltip-icon-button";
 import { Dialog, DialogContent } from "@/components/ui/dialog";
 import { Tabs, TabsContent } from "@/components/ui/tabs";
 import type { SearchSourceConnector } from "@/contracts/types/connector.types";
 import { useConnectorsElectric } from "@/hooks/use-connectors-electric";
 import { useDocumentsElectric } from "@/hooks/use-documents-electric";
+import { useInbox } from "@/hooks/use-inbox";
 import { cn } from "@/lib/utils";
 import { ConnectorDialogHeader } from "./connector-popup/components/connector-dialog-header";
 import { ConnectorConnectView } from "./connector-popup/connector-configs/views/connector-connect-view";
@@ -27,10 +29,18 @@ import { YouTubeCrawlerView } from "./connector-popup/views/youtube-crawler-view
 export const ConnectorIndicator: FC = () => {
 	const searchSpaceId = useAtomValue(activeSearchSpaceIdAtom);
 	const searchParams = useSearchParams();
+	const { data: currentUser } = useAtomValue(currentUserAtom);
 
 	// Fetch document type counts using Electric SQL + PGlite for real-time updates
 	const { documentTypeCounts, loading: documentTypesLoading } = useDocumentsElectric(searchSpaceId);
 
+	// Fetch notifications to detect indexing failures
+	const { inboxItems = [] } = useInbox(
+		currentUser?.id ?? null,
+		searchSpaceId ? Number(searchSpaceId) : null,
+		"connector_indexing"
+	);
+
 	// Check if YouTube view is active
 	const isYouTubeView = searchParams.get("view") === "youtube";
 
@@ -116,8 +126,10 @@ export const ConnectorIndicator: FC = () => {
 	};
 
 	// Track indexing state locally - clears automatically when Electric SQL detects last_indexed_at changed
-	const { indexingConnectorIds, startIndexing } = useIndexingConnectors(
+	// Also clears when failed notifications are detected
-		connectors as SearchSourceConnector[]
+	const { indexingConnectorIds, startIndexing, stopIndexing } = useIndexingConnectors(
+		connectors as SearchSourceConnector[],
+		inboxItems
 	);
 
 	const isLoading = connectorsLoading || documentTypesLoading;
@@ -246,7 +258,7 @@ export const ConnectorIndicator: FC = () => {
 							editingConnector.connector_type !== "GOOGLE_DRIVE_CONNECTOR"
 								? () => {
 										startIndexing(editingConnector.id);
-										handleQuickIndexConnector(editingConnector.id, editingConnector.connector_type);
+										handleQuickIndexConnector(editingConnector.id, editingConnector.connector_type, stopIndexing);
 									}
 								: undefined
 						}

surfsense_web/components/assistant-ui/connector-popup/connector-configs/views/connector-edit-view.tsx

@@ -97,7 +97,7 @@ export const ConnectorEditView: FC<ConnectorEditViewProps> = ({
 		};
 	}, [checkScrollState]);
 
-	// Reset local quick indexing state when indexing completes
+	// Reset local quick indexing state when indexing completes or fails
 	useEffect(() => {
 		if (!isIndexing) {
 			setIsQuickIndexing(false);

surfsense_web/components/assistant-ui/connector-popup/hooks/use-connector-dialog.ts

@@ -1375,7 +1375,7 @@ export const useConnectorDialog = () => {
 
 	// Handle quick index (index without date picker, uses backend defaults)
 	const handleQuickIndexConnector = useCallback(
-		async (connectorId: number, connectorType?: string) => {
+		async (connectorId: number, connectorType?: string, stopIndexing?: (id: number) => void) => {
 			if (!searchSpaceId) return;
 
 			// Track quick index clicked event
@@ -1401,6 +1401,10 @@ export const useConnectorDialog = () => {
 			} catch (error) {
 				console.error("Error indexing connector content:", error);
 				toast.error(error instanceof Error ? error.message : "Failed to start indexing");
+				// Stop indexing state on error
+				if (stopIndexing) {
+					stopIndexing(connectorId);
+				}
 			}
 		},
 		[searchSpaceId, indexConnector]

surfsense_web/components/assistant-ui/connector-popup/hooks/use-indexing-connectors.ts

@@ -2,6 +2,8 @@
 
 import { useCallback, useEffect, useRef, useState } from "react";
 import type { SearchSourceConnector } from "@/contracts/types/connector.types";
+import type { InboxItem } from "@/contracts/types/inbox.types";
+import { isConnectorIndexingMetadata } from "@/contracts/types/inbox.types";
 
 /**
  * Hook to track which connectors are currently indexing using local state.
@@ -9,10 +11,14 @@ import type { SearchSourceConnector } from "@/contracts/types/connector.types";
  * This provides a better UX than polling by:
  * 1. Setting indexing state immediately when user triggers indexing (optimistic)
  * 2. Clearing indexing state when Electric SQL detects last_indexed_at changed
+ * 3. Clearing indexing state when a failed notification is detected
  *
  * The actual `last_indexed_at` value comes from Electric SQL/PGlite, not local state.
  */
-export function useIndexingConnectors(connectors: SearchSourceConnector[]) {
+export function useIndexingConnectors(
+	connectors: SearchSourceConnector[],
+	inboxItems?: InboxItem[]
+) {
 	// Set of connector IDs that are currently indexing
 	const [indexingConnectorIds, setIndexingConnectorIds] = useState<Set<number>>(new Set());
 
@@ -48,6 +54,40 @@ export function useIndexingConnectors(connectors: SearchSourceConnector[]) {
 		}
 	}, [connectors, indexingConnectorIds]);
 
+	// Detect failed notifications and stop indexing state
+	useEffect(() => {
+		if (!inboxItems || inboxItems.length === 0) return;
+
+		const newIndexingIds = new Set(indexingConnectorIds);
+		let hasChanges = false;
+
+		for (const item of inboxItems) {
+			// Only check connector_indexing notifications
+			if (item.type !== "connector_indexing") continue;
+
+			// Check if this notification indicates a failure
+			const metadata = isConnectorIndexingMetadata(item.metadata)
+				? item.metadata
+				: null;
+			if (!metadata) continue;
+
+			// Check if status is "failed" or if there's an error_message
+			const isFailed =
+				metadata.status === "failed" ||
+				(metadata.error_message && metadata.error_message.trim().length > 0);
+
+			// If failed and connector is in indexing state, clear it
+			if (isFailed && indexingConnectorIds.has(metadata.connector_id)) {
+				newIndexingIds.delete(metadata.connector_id);
+				hasChanges = true;
+			}
+		}
+
+		if (hasChanges) {
+			setIndexingConnectorIds(newIndexingIds);
+		}
+	}, [inboxItems, indexingConnectorIds]);
+
 	// Add a connector to the indexing set (called when indexing starts)
 	const startIndexing = useCallback((connectorId: number) => {
 		setIndexingConnectorIds((prev) => {