diff --git a/aiui/packages/app/src/__tests__/fixtures/seedPrompts.ts b/aiui/packages/app/src/__tests__/fixtures/seedPrompts.ts
index 34f1c98e..8e16261a 100644
--- a/aiui/packages/app/src/__tests__/fixtures/seedPrompts.ts
+++ b/aiui/packages/app/src/__tests__/fixtures/seedPrompts.ts
@@ -70,7 +70,12 @@ All feature practical effects, IMAX cinematography, and Hans Zimmer scores (exce
 [[song_ext:Music for Airports 1/1|Brian Eno|1978]] — The track that coined "ambient music." Tape loops of piano and voices create an ever-evolving soundscape.
 
 [[song_ext:Treefingers|Radiohead|2000]] — From Kid A. Processed guitar creating ethereal textures. Works beautifully on loop.`,
-    expected: { songs: 10 },
+    // Six, not ten. The assistantResponse above lists exactly six
+    // `song_ext` entries and ends coherently on Treefingers — it was never
+    // truncated. The extractor was returning the right answer and this
+    // number was the wrong one, which is why "extracts 10 songs" had been
+    // failing. Counted from the fixture, not from intent.
+    expected: { songs: 6 },
   },
 
   // ─── Books ──────────────────────────────────────────────────
diff --git a/aiui/packages/app/src/__tests__/useAI.test.ts b/aiui/packages/app/src/__tests__/useAI.test.ts
index 3a8dfda7..87d2dd1d 100644
--- a/aiui/packages/app/src/__tests__/useAI.test.ts
+++ b/aiui/packages/app/src/__tests__/useAI.test.ts
@@ -348,6 +348,36 @@ describe('useAI', () => {
       const body = JSON.parse(claudeCall![1].body as string)
       expect(body.system).toContain('Web search results')
       expect(body.system).toContain('Result 1')
+      // FALSE on purpose: `proxyWebSearch = webSearchEnabled && !clientSearchSucceeded`.
+      // The client already searched and injected the results above, so asking
+      // the proxy to search again would be a second, redundant search per turn.
+      // This assertion read `true` and had been failing since that change —
+      // the test was stale, the behaviour is intentional.
+      expect(body.webSearch).toBe(false)
+    })
+
+    it('asks the proxy to search when the client-side search finds nothing', async () => {
+      // The other half of the same contract: no client results means nothing
+      // was injected, so the proxy must still do the search.
+      vi.mocked(searchWeb).mockResolvedValue([])
+
+      const fetchSpy = vi.fn().mockResolvedValue(
+        mockClaudeResponse(['data: {"type":"content_block_delta","delta":{"text":"answer"}}\n\n'])
+      )
+      globalThis.fetch = fetchSpy
+
+      const chatStore = useChatStore()
+      chatStore.webSearchEnabled = true
+      const { sendMessage } = useAI()
+
+      await sendMessage('latest bitcoin news')
+
+      const claudeCall = fetchSpy.mock.calls.find(
+        (c: unknown[]) => (c[0] as string)?.toString().includes('/claude/')
+      )
+      expect(claudeCall).toBeDefined()
+      const body = JSON.parse(claudeCall![1].body as string)
+      expect(body.system).not.toContain('Web search results')
       expect(body.webSearch).toBe(true)
     })
   })