llm-fe/src/llm-fe/components/DriveConnectionsSection/DriveConnectionsSection.tsx

@@ -8,9 +8,11 @@ import {
   connectDrive,
   disconnectDriveConnection,
   fetchDriveConnections,
+  formatDriveSyncError,
   parseResourceIdsInput,
   saveDriveResourceSelection,
   syncDriveConnection,
+  waitForDriveSyncSettlement,
 } from "../../utils/drive";
 
 const Section = styled.div`
@@ -171,6 +173,45 @@ const EmptyState = styled.p`
   opacity: 0.6;
 `;
 
+const AlertBanner = styled.div<{ $tone: 'error' | 'success' }>`
+  display: flex;
+  align-items: flex-start;
+  justify-content: space-between;
+  gap: 1rem;
+  margin: 0 0 1.25rem 0;
+  padding: 0.85rem 1rem;
+  border-radius: 0.5rem;
+  border: 1px solid
+    ${({ $tone }) => ($tone === 'error' ? 'rgba(255, 107, 107, 0.45)' : 'rgba(46, 204, 113, 0.45)')};
+  background: ${({ $tone }) =>
+    $tone === 'error' ? 'rgba(255, 71, 87, 0.12)' : 'rgba(46, 204, 113, 0.12)'};
+  color: ${({ theme }) => theme.colors.text};
+  font-size: 0.9rem;
+  line-height: 1.4;
+`;
+
+const AlertDismiss = styled.button`
+  background: transparent;
+  border: none;
+  color: inherit;
+  font-size: 1.25rem;
+  line-height: 1;
+  cursor: pointer;
+  opacity: 0.7;
+  padding: 0;
+
+  &:hover {
+    opacity: 1;
+  }
+`;
+
+const SyncErrorText = styled.p`
+  margin: 0.75rem 0 0 0;
+  font-size: 0.85rem;
+  color: #ff6b6b;
+  line-height: 1.4;
+`;
+
 const PROVIDER_LABELS: Record<DriveProvider, string> = {
   google: "Google Drive",
   microsoft: "OneDrive",
@@ -183,6 +224,7 @@ type DriveConnectionsSectionProps = {
   title: string;
   description?: string;
   connectIntent: DriveConnectIntent;
+  onSynced?: () => void;
 };
 
 const DriveConnectionsSection = ({
@@ -190,11 +232,15 @@ const DriveConnectionsSection = ({
   title,
   description,
   connectIntent,
+  onSynced,
 }: DriveConnectionsSectionProps): JSX.Element => {
   const [connections, setConnections] = useState<DriveConnectionType[]>([]);
   const [loading, setLoading] = useState(true);
   const [loadError, setLoadError] = useState(false);
   const [connectError, setConnectError] = useState<string | null>(null);
+  const [syncBanner, setSyncBanner] = useState<{ tone: 'error' | 'success'; message: string } | null>(
+    null
+  );
   const [resourceInputs, setResourceInputs] = useState<Record<number, string>>({});
   const [pendingAction, setPendingAction] = useState<Record<number, PendingAction | undefined>>({});
 
@@ -219,6 +265,16 @@ const DriveConnectionsSection = ({
     setPendingAction((prev) => ({ ...prev, [id]: action }));
   };
 
+  const upsertConnection = (updated: DriveConnectionType) => {
+    setConnections((prev) => {
+      const exists = prev.some((conn) => conn.id === updated.id);
+      if (!exists) {
+        return (updated.kind || 'personal') === kind ? [...prev, updated] : prev;
+      }
+      return prev.map((conn) => (conn.id === updated.id ? { ...conn, ...updated } : conn));
+    });
+  };
+
   const handleDisconnect = async (id: number) => {
     setAction(id, 'disconnect');
     try {
@@ -226,6 +282,7 @@ const DriveConnectionsSection = ({
       setConnections((prev) => prev.filter((conn) => conn.id !== id));
     } catch (err) {
       console.log(err);
+      setSyncBanner({ tone: 'error', message: 'Could not disconnect this drive. Try again.' });
     } finally {
       setAction(id, undefined);
     }
@@ -233,11 +290,33 @@ const DriveConnectionsSection = ({
 
   const handleSync = async (id: number) => {
     setAction(id, 'sync');
+    setSyncBanner(null);
     try {
-      await syncDriveConnection(id);
-      await loadConnections();
+      const enqueued = await syncDriveConnection(id);
+      upsertConnection(enqueued.connection);
+
+      const settled =
+        enqueued.connection.last_sync_status === 'pending'
+          ? await waitForDriveSyncSettlement(id)
+          : enqueued.connection;
+
+      upsertConnection(settled);
+
+      if (settled.last_sync_status === 'error') {
+        setSyncBanner({
+          tone: 'error',
+          message: formatDriveSyncError(settled.last_sync_error),
+        });
+      } else if (settled.last_sync_status === 'ok') {
+        setSyncBanner({ tone: 'success', message: 'Drive sync finished.' });
+        onSynced?.();
+      }
     } catch (err) {
-      console.log(err);
+      console.error(err);
+      const message =
+        err instanceof Error ? err.message : 'Drive sync failed. Try again.';
+      setSyncBanner({ tone: 'error', message });
+      await loadConnections();
     } finally {
       setAction(id, undefined);
     }
@@ -258,6 +337,7 @@ const DriveConnectionsSection = ({
       setResourceInputs((prev) => ({ ...prev, [id]: '' }));
     } catch (err) {
       console.log(err);
+      setSyncBanner({ tone: 'error', message: 'Could not save folder selection. Try again.' });
     } finally {
       setAction(id, undefined);
     }
@@ -268,6 +348,19 @@ const DriveConnectionsSection = ({
       <SectionTitle>{title}</SectionTitle>
       {description && <SectionDescription>{description}</SectionDescription>}
 
+      {syncBanner && (
+        <AlertBanner $tone={syncBanner.tone} role="alert">
+          <span>{syncBanner.message}</span>
+          <AlertDismiss
+            type="button"
+            aria-label="Dismiss"
+            onClick={() => setSyncBanner(null)}
+          >
+            ×
+          </AlertDismiss>
+        </AlertBanner>
+      )}
+
       <ConnectButtonRow>
         <ConnectButton
           type="button"
@@ -310,6 +403,7 @@ const DriveConnectionsSection = ({
             const selectedLabels = conn.selected_resource_labels?.length
               ? conn.selected_resource_labels
               : conn.selected_resource_ids || [];
+            const isSyncing = action === 'sync' || conn.last_sync_status === 'pending';
 
             return (
               <ConnectionCard key={conn.id}>
@@ -328,9 +422,9 @@ const DriveConnectionsSection = ({
                     <SmallButton
                       type="button"
                       onClick={() => handleSync(conn.id)}
-                      disabled={Boolean(action)}
+                      disabled={Boolean(action) || conn.last_sync_status === 'pending'}
                     >
-                      {action === 'sync' ? 'Syncing…' : 'Sync now'}
+                      {isSyncing ? 'Syncing…' : 'Sync now'}
                     </SmallButton>
                     <DangerButton
                       type="button"
@@ -342,6 +436,10 @@ const DriveConnectionsSection = ({
                   </ConnectionActions>
                 </ConnectionHeader>
 
+                {conn.last_sync_status === 'error' && conn.last_sync_error && (
+                  <SyncErrorText>{formatDriveSyncError(conn.last_sync_error)}</SyncErrorText>
+                )}
+
                 {selectedLabels.length > 0 && (
                   <ResourceTagList>
                     {selectedLabels.map((label, idx) => (

llm-fe/src/llm-fe/pages/DocumentStoragePage/DocumentStoragePage.tsx

@@ -434,6 +434,7 @@ const DocumentStoragePageInner = (): JSX.Element => {
         title="Cloud drives"
         description="Connect your personal Google Drive or OneDrive so its files can be searched in chat."
         connectIntent="link_drive"
+        onSynced={fetchDocuments}
       />
 
       {account?.is_company_manager && (
@@ -442,6 +443,7 @@ const DocumentStoragePageInner = (): JSX.Element => {
           title="Company knowledge sources"
           description="Connect a shared Google Shared Drive or Microsoft 365 site so your whole team can search these files in chat."
           connectIntent="link_company_drive"
+          onSynced={fetchDocuments}
         />
       )}
     </>

llm-fe/src/llm-fe/utils/drive.test.ts

@@ -1,4 +1,8 @@
-import { driveConnectUrl, parseResourceIdsInput } from './drive';
+import {
+  driveConnectUrl,
+  formatDriveSyncError,
+  parseResourceIdsInput,
+} from './drive';
 
 describe('parseResourceIdsInput', () => {
   it('splits comma and newline separated ids and trims whitespace', () => {
@@ -10,6 +14,19 @@ describe('parseResourceIdsInput', () => {
   });
 });
 
+describe('formatDriveSyncError', () => {
+  it('returns a fallback when empty', () => {
+    expect(formatDriveSyncError('')).toMatch(/Drive sync failed/);
+  });
+
+  it('truncates long provider error payloads', () => {
+    const long = 'x'.repeat(400);
+    const formatted = formatDriveSyncError(long, 50);
+    expect(formatted.length).toBeLessThanOrEqual(51);
+    expect(formatted.endsWith('…')).toBe(true);
+  });
+});
+
 describe('driveConnectUrl', () => {
   const originalEnv = process.env.REACT_APP_BACKEND_REST_API_BASE_URL;
 

llm-fe/src/llm-fe/utils/drive.ts

@@ -8,6 +8,8 @@ export type DriveConnectionKind = 'personal' | 'company';
 /** intent query param sent to /auth/oauth/:provider/start/ for drive-linking flows (#83/#84). */
 export type DriveConnectIntent = 'link_drive' | 'link_company_drive';
 
+export type DriveSyncStatus = 'ok' | 'error' | 'pending' | 'never';
+
 export type DriveConnectionType = {
   id: number;
   provider: DriveProvider;
@@ -17,11 +19,16 @@ export type DriveConnectionType = {
   selected_resource_ids?: string[];
   selected_resource_labels?: string[];
   last_sync_at?: string | null;
-  last_sync_status?: string | null;
+  last_sync_status?: DriveSyncStatus | string | null;
   last_sync_error?: string;
   created?: string;
 };
 
+export type DriveSyncEnqueueResponse = {
+  queued?: boolean;
+  connection: DriveConnectionType;
+};
+
 export async function fetchDriveConnections(): Promise<DriveConnectionType[]> {
   const { data } = await axiosInstance.get<DriveConnectionType[]>('/drive/connections/');
   return Array.isArray(data) ? data : [];
@@ -47,12 +54,55 @@ export async function saveDriveResourceSelection(
   return data;
 }
 
-export async function syncDriveConnection(connectionId: number): Promise<DriveConnectionType | null> {
-  const { data } = await axiosInstance.post<{
-    connection?: DriveConnectionType;
-  } & DriveConnectionType>(`/drive/connections/${connectionId}/sync/`);
-  if (!data) return null;
-  return data.connection || data;
+/** Enqueue a Drive sync (#57/#90). Returns quickly with pending status. */
+export async function syncDriveConnection(
+  connectionId: number
+): Promise<DriveSyncEnqueueResponse> {
+  const { data } = await axiosInstance.post<DriveSyncEnqueueResponse>(
+    `/drive/connections/${connectionId}/sync/`
+  );
+  if (!data?.connection) {
+    throw new Error('Drive sync did not return a connection.');
+  }
+  return data;
+}
+
+const DEFAULT_SYNC_POLL_MS = 1500;
+const DEFAULT_SYNC_TIMEOUT_MS = 120_000;
+
+/** Poll connections until the target leaves ``pending`` (or timeout). */
+export async function waitForDriveSyncSettlement(
+  connectionId: number,
+  options?: { intervalMs?: number; timeoutMs?: number }
+): Promise<DriveConnectionType> {
+  const intervalMs = options?.intervalMs ?? DEFAULT_SYNC_POLL_MS;
+  const timeoutMs = options?.timeoutMs ?? DEFAULT_SYNC_TIMEOUT_MS;
+  const deadline = Date.now() + timeoutMs;
+
+  while (Date.now() < deadline) {
+    const connections = await fetchDriveConnections();
+    const connection = connections.find((item) => item.id === connectionId);
+    if (!connection) {
+      throw new Error('Drive connection disappeared while syncing.');
+    }
+    if (connection.last_sync_status !== 'pending') {
+      return connection;
+    }
+    await new Promise((resolve) => setTimeout(resolve, intervalMs));
+  }
+  throw new Error('Drive sync timed out. Check status and try again.');
+}
+
+/** Shorten long provider JSON error blobs for toasts. */
+export function formatDriveSyncError(raw?: string | null, maxLen = 280): string {
+  const text = (raw || '').trim();
+  if (!text) {
+    return 'Drive sync failed. Try again or check provider API settings.';
+  }
+  if (text.length <= maxLen) {
+    return text;
+  }
+  return `${text.slice(0, maxLen).trim()}…`;
 }
 
 /** Absolute backend OAuth start URL for a drive-link flow (personal or company). */