diff --git a/web/mock-server/server.js b/web/mock-server/server.js
index f1c6b18ed..7d9e29e39 100644
--- a/web/mock-server/server.js
+++ b/web/mock-server/server.js
@@ -159,6 +159,15 @@ app.use('/docs', swaggerUi.serve, swaggerUi.setup(mockApiSpec));
 
 // API Routes
 app.get('/api/users/debug/locals', (req, res) => {
+  const cookieHeader = req.headers.cookie ?? '';
+  const tokenMatch = cookieHeader.match(/(?:^|;\s*)token=([^;]+)/);
+  const tokenValue = tokenMatch ? tokenMatch[1] : null;
+
+  if (tokenValue === 'stale-jwt-token') {
+    res.status(401).json({ error: 'Unauthorized' });
+    return;
+  }
+
   res.json({
     locals: {
       owner: 1,
diff --git a/web/src/lib/backend/api.ts b/web/src/lib/backend/api.ts
index 4af4ba710..9f709ec17 100644
--- a/web/src/lib/backend/api.ts
+++ b/web/src/lib/backend/api.ts
@@ -85,7 +85,7 @@ export const get = async (
   if (!response.ok) {
     if (response.status === UNAUTHORIZED) {
       redirectToLogin();
-      return undefined;
+      throw new Error('Unauthorized');
     }
     if (response.status === NOT_FOUND) {
       throw new Error(
diff --git a/web/src/pages/LoginPage/LoginPage.test.tsx b/web/src/pages/LoginPage/LoginPage.test.tsx
new file mode 100644
index 000000000..dd8905912
--- /dev/null
+++ b/web/src/pages/LoginPage/LoginPage.test.tsx
@@ -0,0 +1,108 @@
+import { render, waitFor } from '@testing-library/react';
+import '@testing-library/jest-dom';
+import { describe, it, expect, vi, beforeEach } from 'vitest';
+import { MemoryRouter } from 'react-router-dom';
+import { CookiesProvider } from 'react-cookie';
+import Cookies from 'universal-cookie';
+import { QueryClient, QueryClientProvider } from '@tanstack/react-query';
+import { LoginPage } from './LoginPage';
+
+vi.mock('../../lib/hooks/useUserLocals', () => ({
+  useUserLocals: vi.fn(),
+}));
+
+vi.mock('./components/LoginForm', () => ({
+  default: () => <div data-testid="login-form" />,
+}));
+
+vi.mock('../../components/AuthPageBackground', () => ({
+  AuthPageBackground: ({ children }: { children: React.ReactNode }) => (
+    <div>{children}</div>
+  ),
+}));
+
+import { useUserLocals } from '../../lib/hooks/useUserLocals';
+
+const mockUseUserLocals = useUserLocals as ReturnType<typeof vi.fn>;
+
+function renderLoginPage(cookieValue?: string) {
+  const cookies = new Cookies();
+  if (cookieValue != null) {
+    cookies.set('token', cookieValue, { path: '/' });
+  }
+
+  const queryClient = new QueryClient({
+    defaultOptions: { queries: { retry: false } },
+  });
+
+  return render(
+    <QueryClientProvider client={queryClient}>
+      <CookiesProvider>
+        <MemoryRouter initialEntries={['/login']}>
+          <LoginPage />
+        </MemoryRouter>
+      </CookiesProvider>
+    </QueryClientProvider>
+  );
+}
+
+describe('LoginPage', () => {
+  beforeEach(() => {
+    const cookies = new Cookies();
+    cookies.remove('token', { path: '/' });
+    vi.clearAllMocks();
+  });
+
+  it('renders the login form when there is no cookie', () => {
+    mockUseUserLocals.mockReturnValue({ data: undefined, isLoading: false, isError: false, error: null });
+    const { getByTestId } = renderLoginPage();
+    expect(getByTestId('login-form')).toBeInTheDocument();
+  });
+
+  it('renders the login form when the cookie is valid', () => {
+    mockUseUserLocals.mockReturnValue({
+      data: { user: { id: 1 }, locals: {} },
+      isLoading: false,
+      isError: false,
+      error: null,
+    });
+    const { getByTestId } = renderLoginPage('valid-token');
+    expect(getByTestId('login-form')).toBeInTheDocument();
+  });
+
+  it('clears the token cookie when the cookie is present and userLocals fetch errors', async () => {
+    mockUseUserLocals.mockReturnValue({
+      data: undefined,
+      isLoading: false,
+      isError: true,
+      error: new Error('Unauthorized'),
+    });
+
+    const cookies = new Cookies();
+    cookies.set('token', 'stale-jwt-token', { path: '/' });
+
+    renderLoginPage('stale-jwt-token');
+
+    await waitFor(() => {
+      const tokenCookie = cookies.get('token');
+      expect(tokenCookie).toBeUndefined();
+    });
+  });
+
+  it('does not clear the token cookie when no cookie is present and fetch errors', async () => {
+    mockUseUserLocals.mockReturnValue({
+      data: undefined,
+      isLoading: false,
+      isError: true,
+      error: new Error('Unauthorized'),
+    });
+
+    const cookies = new Cookies();
+
+    renderLoginPage();
+
+    await waitFor(() => {
+      expect(cookies.get('token')).toBeUndefined();
+    });
+  });
+});
diff --git a/web/src/pages/LoginPage/LoginPage.tsx b/web/src/pages/LoginPage/LoginPage.tsx
index 62ea873c5..121c57e54 100644
--- a/web/src/pages/LoginPage/LoginPage.tsx
+++ b/web/src/pages/LoginPage/LoginPage.tsx
@@ -1,7 +1,19 @@
+import { useEffect } from 'react';
+import { useCookies } from 'react-cookie';
 import LoginForm from './components/LoginForm';
 import { AuthPageBackground } from '../../components/AuthPageBackground';
+import { useUserLocals } from '../../lib/hooks/useUserLocals';
 
 export function LoginPage() {
+  const [cookies, , removeCookie] = useCookies(['token']);
+  const { isError } = useUserLocals();
+
+  useEffect(() => {
+    if (cookies.token && isError) {
+      removeCookie('token', { path: '/' });
+    }
+  }, [cookies.token, isError, removeCookie]);
+
   return (
     <AuthPageBackground>
       <LoginForm />
diff --git a/web/tests/login-loop.spec.ts b/web/tests/login-loop.spec.ts
new file mode 100644
index 000000000..b407a8803
--- /dev/null
+++ b/web/tests/login-loop.spec.ts
@@ -0,0 +1,36 @@
+import { test, expect } from '@playwright/test';
+
+test.describe('login-loop prevention', () => {
+  test('clears a stale token cookie and renders the login form without looping', async ({
+    page,
+    context,
+  }) => {
+    await context.addCookies([
+      {
+        name: 'token',
+        value: 'stale-jwt-token',
+        domain: 'localhost',
+        path: '/',
+        httpOnly: false,
+        secure: false,
+        sameSite: 'Lax',
+      },
+    ]);
+
+    await page.goto('/login');
+
+    await expect(page.locator('h1')).toContainText('Log in', {
+      timeout: 10_000,
+    });
+
+    await expect
+      .poll(
+        async () => {
+          const cookies = await context.cookies();
+          return cookies.find((c) => c.name === 'token');
+        },
+        { timeout: 15_000, intervals: [500] }
+      )
+      .toBeUndefined();
+  });
+});