diff --git a/.app.pid b/.app.pid
index d58c2d5..cdfc4e6 100644
--- a/.app.pid
+++ b/.app.pid
@@ -1 +1 @@
-249378
+267794
diff --git a/src/lib/googleAuth.ts b/src/lib/googleAuth.ts
index 9ddafa2..d5b8191 100644
--- a/src/lib/googleAuth.ts
+++ b/src/lib/googleAuth.ts
@@ -1,9 +1,33 @@
 import { JobApplication } from '../types';
 
 let cachedAccessToken: string | null = localStorage.getItem('ai_job_portal_google_token');
+let tokenExpiresAt: number = Number(localStorage.getItem('ai_job_portal_google_token_exp') || '0');
 
 export const getCachedAccessToken = () => cachedAccessToken;
 
+/**
+ * Silent / Interactive Token Refresh Mechanism
+ * Automatically checks token age and triggers silent OAuth popup or re-auth if token is expired.
+ */
+export const ensureValidAccessToken = async (): Promise<string | null> => {
+  const now = Date.now();
+
+  // If token exists and is valid for at least another 3 minutes, reuse it
+  if (cachedAccessToken && tokenExpiresAt > now + 3 * 60 * 1000) {
+    return cachedAccessToken;
+  }
+
+  // Token is expired or expiring soon -> Trigger silent refresh / prompt-less re-auth
+  console.log('[Google Auth] OAuth Token expired or expiring soon. Triggering automatic token refresh...');
+  try {
+    const authResult = await googleWorkspaceSignIn(true); // silent = true
+    return authResult.accessToken;
+  } catch (err: any) {
+    console.warn('[Google Auth] Silent token refresh notice:', err.message);
+    return cachedAccessToken;
+  }
+};
+
 const getEnvVar = (key: string) => {
   try {
     return (import.meta as any).env?.[key];
@@ -18,12 +42,13 @@ const OAUTH_CLIENT_ID = getEnvVar('VITE_GOOGLE_OAUTH_CLIENT_ID') || '48854802845
  * Direct Google OAuth 2.0 Flow via Google Identity Services
  * Obtains real access token directly from accounts.google.com for Google Drive/Sheets API calls.
  */
-export const googleWorkspaceSignIn = async (): Promise<{ email: string; name: string; accessToken: string }> => {
+export const googleWorkspaceSignIn = async (silentMode: boolean = false): Promise<{ email: string; name: string; accessToken: string }> => {
   return new Promise((resolve, reject) => {
     try {
       const scope = encodeURIComponent('https://www.googleapis.com/auth/spreadsheets https://www.googleapis.com/auth/drive https://www.googleapis.com/auth/documents');
       const redirectUri = encodeURIComponent(`${window.location.origin}`);
-      const authUrl = `https://accounts.google.com/o/oauth2/v2/auth?client_id=${OAUTH_CLIENT_ID}&redirect_uri=${redirectUri}&response_type=token&scope=${scope}&prompt=select_account`;
+      const promptParam = silentMode ? 'none' : 'select_account';
+      const authUrl = `https://accounts.google.com/o/oauth2/v2/auth?client_id=${OAUTH_CLIENT_ID}&redirect_uri=${redirectUri}&response_type=token&scope=${scope}&prompt=${promptParam}`;
 
       const width = 500;
       const height = 650;
@@ -59,10 +84,14 @@ export const googleWorkspaceSignIn = async (): Promise<{ email: string; name: st
 
               const params = new URLSearchParams(hash.substring(1));
               const token = params.get('access_token');
+              const expiresInSeconds = Number(params.get('expires_in') || '3600');
+              const expiresAt = Date.now() + expiresInSeconds * 1000;
 
               if (token) {
                 cachedAccessToken = token;
+                tokenExpiresAt = expiresAt;
                 localStorage.setItem('ai_job_portal_google_token', token);
+                localStorage.setItem('ai_job_portal_google_token_exp', String(expiresAt));
                 localStorage.setItem('ai_job_portal_google_connected', 'true');
 
                 try {
@@ -99,20 +128,20 @@ export const googleWorkspaceSignIn = async (): Promise<{ email: string; name: st
 
 export const googleSignOut = async () => {
   cachedAccessToken = null;
+  tokenExpiresAt = 0;
   localStorage.removeItem('ai_job_portal_google_token');
+  localStorage.removeItem('ai_job_portal_google_token_exp');
   localStorage.removeItem('ai_job_portal_google_connected');
   localStorage.removeItem('ai_job_portal_google_user');
 };
 
-
-
 // Workspace Action Handlers
 
 export async function exportApplicationsToGoogleSheets(
   applications: JobApplication[],
   accessToken?: string
 ): Promise<{ spreadsheetId: string; spreadsheetUrl: string; isLocalCsv?: boolean; message?: string }> {
-  const token = accessToken || cachedAccessToken;
+  const token = accessToken || (await ensureValidAccessToken()) || cachedAccessToken;
   const res = await fetch('/api/workspace/sheets/export', {
     method: 'POST',
     headers: {
@@ -134,7 +163,7 @@ export async function createTailoredGoogleDoc(
   docType: 'resume' | 'coverLetter' | 'note',
   accessToken?: string
 ): Promise<{ documentId: string; documentUrl: string; isLocalDoc?: boolean; message?: string }> {
-  const token = accessToken || cachedAccessToken;
+  const token = accessToken || (await ensureValidAccessToken()) || cachedAccessToken;
   const res = await fetch('/api/workspace/docs/create', {
     method: 'POST',
     headers: {
@@ -156,7 +185,7 @@ export async function uploadFileToGoogleDrive(
   mimeType: string = 'text/plain',
   accessToken?: string
 ): Promise<{ fileId: string; driveUrl: string; isLocalFile?: boolean; message?: string }> {
-  const token = accessToken || cachedAccessToken;
+  const token = accessToken || (await ensureValidAccessToken()) || cachedAccessToken;
   const res = await fetch('/api/workspace/drive/upload', {
     method: 'POST',
     headers: {