diff --git a/app/auth/security.py b/app/auth/security.py
index 11cd303..cdc49f2 100644
--- a/app/auth/security.py
+++ b/app/auth/security.py
@@ -38,7 +38,10 @@ def create_access_token(data: dict, expires_delta: Optional[timedelta] = None) -
     else:
         expire = datetime.utcnow() + timedelta(minutes=settings.access_token_expire_minutes)
     
-    to_encode.update({"exp": expire})
+    to_encode.update({
+        "exp": expire,
+        "iat": datetime.utcnow(),
+    })
     encoded_jwt = jwt.encode(to_encode, settings.secret_key, algorithm=settings.algorithm)
     return encoded_jwt
 
@@ -46,7 +49,12 @@ def create_access_token(data: dict, expires_delta: Optional[timedelta] = None) -
 def verify_token(token: str) -> Optional[str]:
     """Verify JWT token and return username"""
     try:
-        payload = jwt.decode(token, settings.secret_key, algorithms=[settings.algorithm])
+        payload = jwt.decode(
+            token,
+            settings.secret_key,
+            algorithms=[settings.algorithm],
+            leeway=30  # allow small clock skew
+        )
         username: str = payload.get("sub")
         if username is None:
             return None
diff --git a/static/js/main.js b/static/js/main.js
index c1cfffd..ef69b3e 100644
--- a/static/js/main.js
+++ b/static/js/main.js
@@ -6,7 +6,9 @@
 const app = {
     token: localStorage.getItem('auth_token'),
     user: null,
-    initialized: false
+    initialized: false,
+    refreshTimerId: null,
+    refreshInProgress: false
 };
 
 // Initialize application
@@ -20,7 +22,7 @@ async function initializeApp() {
         window.keyboardShortcuts.initialize();
     }
     
-    // Remove Bootstrap-dependent tooltips/popovers; use native title/tooltips if needed
+    // Tooltips/popovers handled via native browser features as needed
     
     // Add form validation classes
     initializeFormValidation();
@@ -34,7 +36,7 @@ async function initializeApp() {
 
 // Form validation
 function initializeFormValidation() {
-    // Native validation handling without Bootstrap classes
+    // Native validation handling
     const forms = document.querySelectorAll('form');
     forms.forEach(form => {
         form.addEventListener('submit', function(event) {
@@ -72,20 +74,50 @@ function setupAPIHelpers() {
     if (app.token) {
         window.apiHeaders['Authorization'] = `Bearer ${app.token}`;
     }
+
+    // Start proactive refresh scheduling when a token is present
+    if (app.token) {
+        scheduleTokenRefresh();
+    }
 }
 
 // API utility functions
 async function apiCall(url, options = {}) {
+    // Proactively refresh token if close to expiry
+    if (app.token) {
+        const msLeft = getMsUntilExpiry(app.token);
+        if (msLeft !== null && msLeft < 5 * 60 * 1000) { // < 5 minutes
+            try {
+                await refreshToken();
+            } catch (e) {
+                logout();
+                throw new Error('Authentication required');
+            }
+        }
+    }
+
     const config = {
         headers: { ...window.apiHeaders, ...options.headers },
         ...options
     };
     
     try {
-        const response = await fetch(url, config);
+        let response = await fetch(url, config);
         
+        if (response.status === 401 && app.token) {
+            // Attempt one refresh then retry once
+            try {
+                await refreshToken();
+                const retryConfig = {
+                    headers: { ...window.apiHeaders, ...options.headers },
+                    ...options
+                };
+                response = await fetch(url, retryConfig);
+            } catch (_) {
+                // fall through to logout below
+            }
+        }
         if (response.status === 401) {
-            // Token expired or invalid
             logout();
             throw new Error('Authentication required');
         }
@@ -130,9 +162,17 @@ function setAuthToken(token) {
     app.token = token;
     localStorage.setItem('auth_token', token);
     window.apiHeaders['Authorization'] = `Bearer ${token}`;
+
+    // Reschedule refresh on token update
+    scheduleTokenRefresh();
 }
 
 function logout() {
+    if (app.refreshTimerId) {
+        clearTimeout(app.refreshTimerId);
+        app.refreshTimerId = null;
+    }
+    app.refreshInProgress = false;
     app.token = null;
     app.user = null;
     localStorage.removeItem('auth_token');
@@ -363,4 +403,68 @@ window.apiPost = apiPost;
 window.apiPut = apiPut;
 window.apiDelete = apiDelete;
 window.formatCurrency = formatCurrency;
-window.formatDate = formatDate;
\ No newline at end of file
+window.formatDate = formatDate;
+
+// JWT utilities and refresh handling
+function decodeJwt(token) {
+    try {
+        const payload = token.split('.')[1];
+        const json = atob(payload.replace(/-/g, '+').replace(/_/g, '/'));
+        return JSON.parse(json);
+    } catch (e) {
+        return null;
+    }
+}
+
+function getMsUntilExpiry(token) {
+    const decoded = decodeJwt(token);
+    if (!decoded || !decoded.exp) return null;
+    const expiryMs = decoded.exp * 1000;
+    return expiryMs - Date.now();
+}
+
+function scheduleTokenRefresh() {
+    if (!app.token) return;
+
+    // Clear existing timer
+    if (app.refreshTimerId) {
+        clearTimeout(app.refreshTimerId);
+        app.refreshTimerId = null;
+    }
+
+    const msLeft = getMsUntilExpiry(app.token);
+    if (msLeft === null) return;
+
+    // Refresh 5 minutes before expiry, but not sooner than 30 seconds from now
+    const leadTimeMs = 5 * 60 * 1000;
+    const refreshInMs = Math.max(msLeft - leadTimeMs, 30 * 1000);
+
+    app.refreshTimerId = setTimeout(() => {
+        // Fire and forget; apiCall path also guards per-request
+        refreshToken().catch(() => {
+            logout();
+        });
+    }, refreshInMs);
+}
+
+async function refreshToken() {
+    if (!app.token) throw new Error('No token to refresh');
+    if (app.refreshInProgress) return; // Avoid parallel refreshes
+    app.refreshInProgress = true;
+    try {
+        const response = await fetch('/api/auth/refresh', {
+            method: 'POST',
+            headers: { ...window.apiHeaders }
+        });
+        if (!response.ok) {
+            throw new Error('Refresh failed');
+        }
+        const data = await response.json();
+        if (!data || !data.access_token) {
+            throw new Error('Invalid refresh response');
+        }
+        setAuthToken(data.access_token);
+    } finally {
+        app.refreshInProgress = false;
+    }
+}
\ No newline at end of file