diff --git a/web-dashboard/src/components/trading/OrdersTable.tsx b/web-dashboard/src/components/trading/OrdersTable.tsx
index 1e0aef2d5..8c11a8df7 100644
--- a/web-dashboard/src/components/trading/OrdersTable.tsx
+++ b/web-dashboard/src/components/trading/OrdersTable.tsx
@@ -98,9 +98,14 @@ function OrderRow({ order }: { order: Order }) {
             disabled={cancelOrder.isPending}
             className="px-2 py-0.5 text-xs rounded bg-[var(--color-red)]/20 text-[var(--color-red)] hover:bg-[var(--color-red)]/30 disabled:opacity-50"
           >
-            Cancel
+            {cancelOrder.isPending ? 'Cancelling...' : 'Cancel'}
           </button>
         )}
+        {cancelOrder.isError && (
+          <span className="text-xs text-[var(--color-red)]">
+            {cancelOrder.error.message}
+          </span>
+        )}
       </td>
     </tr>
   );
diff --git a/web-dashboard/src/lib/api.ts b/web-dashboard/src/lib/api.ts
index 4aca026cb..c089d7dd0 100644
--- a/web-dashboard/src/lib/api.ts
+++ b/web-dashboard/src/lib/api.ts
@@ -1,7 +1,20 @@
-import { clearTokens } from './auth';
+import { clearTokens, isTokenExpired, SESSION_EXPIRED_KEY } from './auth';
 
 const API_BASE = import.meta.env.VITE_API_URL ?? '/api';
 
+/** Margin in seconds before actual expiry to treat the token as expired */
+const EXPIRY_MARGIN_SECONDS = 60;
+
+/**
+ * Redirect to login with a session-expired flag so the LoginPage can
+ * display a user-friendly message instead of a silent redirect.
+ */
+function redirectToLogin(): void {
+  sessionStorage.setItem(SESSION_EXPIRED_KEY, '1');
+  clearTokens();
+  window.location.href = '/login';
+}
+
 /** Fetch wrapper that injects JWT Authorization header and handles 401 auto-logout */
 async function apiFetch<T>(
   path: string,
@@ -9,6 +22,12 @@ async function apiFetch<T>(
 ): Promise<T> {
   const token = localStorage.getItem('foxhunt_token');
 
+  // Pre-flight: detect expired (or about-to-expire) tokens before making the request
+  if (token && isTokenExpired(token, EXPIRY_MARGIN_SECONDS)) {
+    redirectToLogin();
+    throw new Error('Session expired. Please log in again.');
+  }
+
   const headers: Record<string, string> = {
     'Content-Type': 'application/json',
     ...(options.headers as Record<string, string> ?? {}),
@@ -24,10 +43,9 @@ async function apiFetch<T>(
   });
 
   if (!res.ok) {
-    // Auto-logout on 401 (expired/invalid token)
+    // Server rejected the token — redirect gracefully
     if (res.status === 401) {
-      clearTokens();
-      window.location.href = '/login';
+      redirectToLogin();
       throw new Error('Session expired. Please log in again.');
     }
 
diff --git a/web-dashboard/src/lib/auth.ts b/web-dashboard/src/lib/auth.ts
index ab60723ca..a4ce42574 100644
--- a/web-dashboard/src/lib/auth.ts
+++ b/web-dashboard/src/lib/auth.ts
@@ -33,6 +33,26 @@ export function isAuthenticated(): boolean {
   }
 }
 
+/** Get the expiry timestamp (seconds since epoch) from a JWT, or null if undecodable */
+export function getTokenExpiry(token: string): number | null {
+  try {
+    const payload = JSON.parse(atob(token.split('.')[1]));
+    return typeof payload.exp === 'number' ? payload.exp : null;
+  } catch {
+    return null;
+  }
+}
+
+/** Check whether a JWT token is expired or within `marginSeconds` of expiry */
+export function isTokenExpired(token: string, marginSeconds = 0): boolean {
+  const exp = getTokenExpiry(token);
+  if (exp === null) return true; // treat undecodable tokens as expired
+  return exp - marginSeconds <= Date.now() / 1000;
+}
+
+/** Session-expired flag key for sessionStorage */
+export const SESSION_EXPIRED_KEY = 'session_expired';
+
 /** Decode JWT claims without verification (for display purposes) */
 export function getTokenClaims(): { sub: string; roles: string[] } | null {
   const token = getToken();
diff --git a/web-dashboard/src/pages/LoginPage.tsx b/web-dashboard/src/pages/LoginPage.tsx
index 5dcb804d8..81b664706 100644
--- a/web-dashboard/src/pages/LoginPage.tsx
+++ b/web-dashboard/src/pages/LoginPage.tsx
@@ -2,15 +2,24 @@ import { useState, type FormEvent } from 'react';
 import { useNavigate } from 'react-router-dom';
 import { useAuth } from '../hooks/useAuth';
 import { apiPost } from '../lib/api';
+import { SESSION_EXPIRED_KEY } from '../lib/auth';
 
 interface LoginResponse {
   token: string;
   refresh_token?: string;
 }
 
+/** Read and clear the session-expired flag set by the API client on 401 / token expiry */
+function consumeSessionExpiredFlag(): boolean {
+  const expired = sessionStorage.getItem(SESSION_EXPIRED_KEY) === '1';
+  if (expired) sessionStorage.removeItem(SESSION_EXPIRED_KEY);
+  return expired;
+}
+
 export function LoginPage() {
   const [username, setUsername] = useState('');
   const [password, setPassword] = useState('');
+  const [sessionExpired] = useState(consumeSessionExpiredFlag);
   const [error, setError] = useState<string | null>(null);
   const [loading, setLoading] = useState(false);
   const { login, authenticated } = useAuth();
@@ -50,6 +59,12 @@ export function LoginPage() {
           Sign in to access the dashboard
         </p>
 
+        {sessionExpired && (
+          <p className="text-xs text-[var(--color-yellow,#ca8a04)] bg-[var(--color-bg-primary)] border border-[var(--color-border)] rounded px-3 py-2 mb-4 text-center">
+            Your session has expired. Please sign in again.
+          </p>
+        )}
+
         <form onSubmit={handleSubmit} className="space-y-4">
           <div>
             <label className="block text-xs text-[var(--color-text-secondary)] mb-1">