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diff --git a/web/test/enable-notifications.test.mjs b/web/test/enable-notifications.test.mjs
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+++ b/web/test/enable-notifications.test.mjs
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+// enable-notifications.test.mjs — Tests for the enableNotifications subscription flow.
+//
+// Run with: node --test web/test/enable-notifications.test.mjs
+
+import { describe, it, beforeEach } from 'node:test';
+import assert from 'node:assert/strict';
+
+// ── Logic under test ──────────────────────────────────────────────────────────
+//
+// When subscribing to push notifications, any existing stale subscription
+// (e.g. from before a VAPID key rotation) must be unsubscribed first.
+// Otherwise the browser rejects subscribe() with "applicationServerKey is not valid".
+
+/**
+ * Extracted subscription logic (mirrors enableNotifications in app.js).
+ * Returns the new subscription endpoint, or throws on error.
+ */
+async function subscribeWithUnsubscribeStale(pushManager, applicationServerKey) {
+  // Clear any stale existing subscription.
+  const existing = await pushManager.getSubscription();
+  if (existing) {
+    await existing.unsubscribe();
+  }
+  const sub = await pushManager.subscribe({ userVisibleOnly: true, applicationServerKey });
+  return sub;
+}
+
+describe('subscribeWithUnsubscribeStale', () => {
+  it('unsubscribes existing subscription before subscribing', async () => {
+    let unsubscribeCalled = false;
+    const existingSub = {
+      unsubscribe: async () => { unsubscribeCalled = true; },
+    };
+    let subscribeCalled = false;
+    const pushManager = {
+      getSubscription: async () => existingSub,
+      subscribe: async (opts) => {
+        subscribeCalled = true;
+        return { endpoint: 'https://push.example.com/sub/new', toJSON: () => ({}) };
+      },
+    };
+
+    await subscribeWithUnsubscribeStale(pushManager, new Uint8Array([4, 1, 2]));
+
+    assert.equal(unsubscribeCalled, true, 'existing subscription should have been unsubscribed');
+    assert.equal(subscribeCalled, true, 'new subscription should have been created');
+  });
+
+  it('subscribes normally when no existing subscription', async () => {
+    let subscribeCalled = false;
+    const pushManager = {
+      getSubscription: async () => null,
+      subscribe: async (opts) => {
+        subscribeCalled = true;
+        return { endpoint: 'https://push.example.com/sub/new', toJSON: () => ({}) };
+      },
+    };
+
+    const sub = await subscribeWithUnsubscribeStale(pushManager, new Uint8Array([4, 1, 2]));
+
+    assert.equal(subscribeCalled, true, 'subscribe should have been called');
+    assert.ok(sub, 'subscription object should be returned');
+  });
+});