diff --git a/src/renderer/src/components/native-chat/use-structured-agent-session-conversation-stop.test.tsx b/src/renderer/src/components/native-chat/use-structured-agent-session-conversation-stop.test.tsx
index e3e22070f79..4724de5b4bd 100644
--- a/src/renderer/src/components/native-chat/use-structured-agent-session-conversation-stop.test.tsx
+++ b/src/renderer/src/components/native-chat/use-structured-agent-session-conversation-stop.test.tsx
@@ -282,4 +282,29 @@ describe("a conversation Stop's first press", () => {
     await pressWithStamp({ kind: 'not-done', notice: 'No.', answered: true }, true)
     expect(toast.error).toHaveBeenCalledExactlyOnceWith('No.')
   })
+
+  it('says a refusal that answers a resend, after a quiet lost answer on the press', async () => {
+    const outcomes: StructuredAgentSessionWriteOutcome<unknown>[] = [
+      { kind: 'not-done', notice: 'Lost.', answered: false },
+      { kind: 'not-done', notice: "The agent wasn't stopped.", answered: true }
+    ]
+    const writeAs = vi.fn<StopWrite>(async () => outcomes.shift() ?? DONE)
+    const { view, stopOutbox } = harness(writeAs)
+    let pressed: Promise<void> = Promise.resolve()
+    act(() => {
+      pressed = view.result.current()
+    })
+    view.rerender({ outbox: [stamped(stopOutbox.mock.calls[0]?.[0])], submissions: [] })
+    await act(async () => {
+      await pressed
+    })
+    for (let step = 0; step < 5; step += 1) {
+      await act(async () => {
+        await vi.advanceTimersByTimeAsync(1_000)
+      })
+    }
+    // The mock outbox keeps the stamp owed, so the Stop may go once more; its answer is said once.
+    expect(writeAs.mock.calls.length).toBeGreaterThanOrEqual(2)
+    expect(toast.error).toHaveBeenCalledExactlyOnceWith("The agent wasn't stopped.")
+  })
 })
diff --git a/src/renderer/src/components/native-chat/use-structured-agent-session-conversation-stop.ts b/src/renderer/src/components/native-chat/use-structured-agent-session-conversation-stop.ts
index 689436a13e7..4f3fed950e9 100644
--- a/src/renderer/src/components/native-chat/use-structured-agent-session-conversation-stop.ts
+++ b/src/renderer/src/components/native-chat/use-structured-agent-session-conversation-stop.ts
@@ -102,12 +102,17 @@ export function useStructuredAgentSessionConversationStop(args: {
           recordStopAnswer(stopOperationId, { kind: 'answered', cursor: outcome.cursor })
           return
         }
-        // A refusal is said; a lost answer only when nothing will send the Stop again.
+        // A refusal is said on any attempt, a resend's too; a lost answer only on the press, and
+        // only when nothing will send the Stop again.
         if (
           outcome.kind === 'not-done' &&
-          firstPress &&
           (outcome.answered ||
-            !stopWillBeResent(latest.current.outbox, latest.current.submissions, stopOperationId))
+            (firstPress &&
+              !stopWillBeResent(
+                latest.current.outbox,
+                latest.current.submissions,
+                stopOperationId
+              )))
         ) {
           toast.error(outcome.notice)
         }