diff --git a/public/sw.js b/public/sw.js
index bf4cb219b..6f60af19c 100644
--- a/public/sw.js
+++ b/public/sw.js
@@ -1,4 +1,4 @@
-const CACHE_VERSION = 'debate-lab-v3';
+const CACHE_VERSION = 'debate-lab-v4';
 const APP_SHELL_CACHE = `${CACHE_VERSION}-shell`;
 const RUNTIME_CACHE = `${CACHE_VERSION}-runtime`;
 
@@ -47,13 +47,22 @@ self.addEventListener('activate', (event) => {
   );
 });
 
+function htmlMislabeledAsAsset(response, request) {
+  const type = (response.headers.get('content-type') || '').toLowerCase();
+  if (!type.includes('text/html')) return false;
+  const path = new URL(request.url).pathname;
+  return request.destination === 'script'
+    || request.destination === 'style'
+    || path.startsWith('/assets/');
+}
+
 async function cacheFirst(request) {
   const cached = await caches.match(request, { ignoreVary: true });
-  if (cached) return cached;
+  if (cached && !htmlMislabeledAsAsset(cached, request)) return cached;
 
   try {
     const response = await fetch(request);
-    if (response.ok) {
+    if (response.ok && !htmlMislabeledAsAsset(response, request)) {
       const cache = await caches.open(RUNTIME_CACHE);
       await cache.put(request, response.clone());
     }
diff --git a/src/lib/reload-stale-chunk.ts b/src/lib/reload-stale-chunk.ts
new file mode 100644
index 000000000..82f39bd98
--- /dev/null
+++ b/src/lib/reload-stale-chunk.ts
@@ -0,0 +1,25 @@
+const RELOAD_PREFIX = 'debatelab-stale-chunk:';
+
+type ReloadTarget = Pick<Window, 'addEventListener' | 'sessionStorage' | 'location'>;
+
+/**
+ * After a deploy, an open tab can ask for a chunk the new build no longer has.
+ * Reload once so the fresh document loads the new names. A second failure on
+ * the same path stays put, so a missing file cannot refresh the tab forever.
+ */
+export function installStaleChunkReload(target: ReloadTarget = window): void {
+  target.addEventListener('vite:preloadError', (event) => {
+    const path = target.location.pathname || '/';
+    const key = `${RELOAD_PREFIX}${path}`;
+    let alreadyReloaded = false;
+    try {
+      alreadyReloaded = target.sessionStorage.getItem(key) === '1';
+      if (!alreadyReloaded) target.sessionStorage.setItem(key, '1');
+    } catch {
+      return;
+    }
+    if (alreadyReloaded) return;
+    event.preventDefault();
+    target.location.reload();
+  });
+}
diff --git a/src/main.tsx b/src/main.tsx
index fb7e1d7a2..400423e09 100644
--- a/src/main.tsx
+++ b/src/main.tsx
@@ -6,6 +6,7 @@ import "./i18n";
 import "@fontsource-variable/inter";
 import "./index.css";
 import { registerServiceWorker } from "./register-service-worker";
+import { installStaleChunkReload } from "./lib/reload-stale-chunk";
 import { initializeObservability } from "./lib/observability";
 import { preloadRoute } from "./lib/route-modules";
 
@@ -24,6 +25,8 @@ function prerenderedRoute(container: HTMLElement): string | undefined {
   return route === "*" || route === window.location.pathname ? route : undefined;
 }
 
+installStaleChunkReload();
+
 export function mountApp(): void {
   const container = document.getElementById("root")!;
   const root = createRoot(container);
diff --git a/src/test/lib/reload-stale-chunk.test.ts b/src/test/lib/reload-stale-chunk.test.ts
new file mode 100644
index 000000000..9189f47b6
--- /dev/null
+++ b/src/test/lib/reload-stale-chunk.test.ts
@@ -0,0 +1,42 @@
+import { describe, expect, it, vi } from 'vitest';
+import { installStaleChunkReload } from '@/lib/reload-stale-chunk';
+
+function fakeWindow() {
+  const listeners = new Map<string, (event: Event) => void>();
+  const stored = new Map<string, string>();
+  const reload = vi.fn();
+  const target = {
+    addEventListener: (type: string, listener: EventListener): void => {
+      listeners.set(type, listener as (event: Event) => void);
+    },
+    sessionStorage: {
+      getItem: (key: string): string | null => stored.get(key) ?? null,
+      setItem: (key: string, value: string): void => { stored.set(key, value); },
+      removeItem: (key: string): void => { stored.delete(key); },
+      clear: (): void => { stored.clear(); },
+      key: (): string | null => null,
+      length: 0,
+    },
+    location: { pathname: '/app/ask', reload },
+  };
+  return { target, listeners, reload };
+}
+
+describe('stale chunk reload', () => {
+  it('reloads once when a route chunk is missing and then lets the error stand', () => {
+    const { target, listeners, reload } = fakeWindow();
+    installStaleChunkReload(target as unknown as Window);
+    const handler = listeners.get('vite:preloadError');
+    expect(handler).toBeTypeOf('function');
+
+    const first = new Event('vite:preloadError', { cancelable: true });
+    handler!(first);
+    expect(first.defaultPrevented).toBe(true);
+    expect(reload).toHaveBeenCalledTimes(1);
+
+    const second = new Event('vite:preloadError', { cancelable: true });
+    handler!(second);
+    expect(second.defaultPrevented).toBe(false);
+    expect(reload).toHaveBeenCalledTimes(1);
+  });
+});
diff --git a/src/test/vercel-deployment-config.test.ts b/src/test/vercel-deployment-config.test.ts
index 4927c7854..a9fc34eb1 100644
--- a/src/test/vercel-deployment-config.test.ts
+++ b/src/test/vercel-deployment-config.test.ts
@@ -183,6 +183,7 @@ describe("Vercel frontend deployment configuration", () => {
     expect(serviceWorker).not.toContain("'/app/sparring'");
     expect(serviceWorker).toContain("'/favicon-72.png'");
     expect(serviceWorker).toContain('cache.put(request, response.clone())');
+    expect(serviceWorker).toContain('htmlMislabeledAsAsset');
     expect(serviceWorker).not.toContain('self.skipWaiting()');
   });