diff --git a/src/renderer/src/components/native-chat/use-structured-agent-session-outbox-unconfirmed-probe.ts b/src/renderer/src/components/native-chat/use-structured-agent-session-outbox-unconfirmed-probe.ts
index 723c8d3ddbe..89cf7834a5a 100644
--- a/src/renderer/src/components/native-chat/use-structured-agent-session-outbox-unconfirmed-probe.ts
+++ b/src/renderer/src/components/native-chat/use-structured-agent-session-outbox-unconfirmed-probe.ts
@@ -1,6 +1,7 @@
 import { useEffect, useLayoutEffect, useRef } from 'react'
 import type { AgentJournalSubmission } from '../../../../shared/agent-session-journal-types'
 import type { StructuredAgentSessionOutboxEntry } from '../../../../shared/structured-agent-session-outbox'
+import { admitStructuredAgentSessionOutboxEntry } from '../../../../shared/structured-agent-session-outbox-admission'
 import { structuredAgentSessionEntryResendsUnconfirmed } from '../../../../shared/structured-agent-session-outbox-unconfirmed-resend'
 import {
   STRUCTURED_AGENT_SESSION_SEND_UNCONFIRMED_WORDS,
@@ -32,9 +33,10 @@ export function useStructuredAgentSessionOutboxUnconfirmedProbe(args: {
 
   // A send with no answer may never have reached the host, and nothing else moves it out of
   // `unconfirmed`, so one would wedge the whole FIFO queue. The same id again is idempotent: the
-  // host replays a recorded answer or performs a genuine first delivery. The first `unconfirmed`
-  // entry is the one holding the queue, at whatever index it sits.
-  const blocker = outbox.find((entry) => entry.state === 'unconfirmed')
+  // host replays a recorded answer or performs a genuine first delivery. The entry the queue's
+  // admission is blocked on is the one resent, never one a Stop outran or an older build left.
+  const admission = admitStructuredAgentSessionOutboxEntry(outbox)
+  const blocker = admission.state === 'blocked' ? admission.entry : undefined
   // The delivery notices read the same rule: while it is resent here, its row says it is sending.
   // Primitives only: `submissions` is rebuilt on every streaming batch, and an array-identity dep
   // would reset the backoff forever while the agent is working.
diff --git a/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.stop-stamp.test.tsx b/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.stop-stamp.test.tsx
index 94852029e92..3c038ecbbeb 100644
--- a/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.stop-stamp.test.tsx
+++ b/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.stop-stamp.test.tsx
@@ -227,6 +227,64 @@ describe('a send a Stop outran', () => {
   })
 })
 
+describe('a Stop answered while the journal is already read through it', () => {
+  it('an idle Stop answered at the cursor already held settles the send with no new journal batch', async () => {
+    seedAttempted()
+    const props: Props = { fence: 1, submissions: [], journalCursor: { epoch: 'e', sequence: 7 } }
+    const view = mount(props)
+    act(() => view.result.current.stop('stop-1'))
+    // An idle host writes nothing for a Stop, so its answer's cursor is the head already loaded.
+    act(() =>
+      view.result.current.recordStopAnswer('stop-1', {
+        kind: 'answered',
+        cursor: { epoch: 'e', sequence: 7 }
+      })
+    )
+    view.rerender(props)
+    expect(view.result.current.outbox).toEqual([])
+    expect(readNativeChatDraftCache(SCOPE)).toBe('follow-up')
+    expect(view.result.current.error).toBeNull()
+    expect(mocks.call).not.toHaveBeenCalled()
+  })
+
+  it('a refused Stop with the journal already loaded settles the send with no new journal batch', async () => {
+    seedAttempted()
+    const props: Props = { fence: 1, submissions: [], journalCursor: { epoch: 'e', sequence: 7 } }
+    const view = mount(props)
+    act(() => view.result.current.stop('stop-1'))
+    act(() => view.result.current.recordStopAnswer('stop-1', { kind: 'unanswerable' }))
+    view.rerender(props)
+    expect(view.result.current.outbox).toEqual([])
+    expect(readNativeChatDraftCache(SCOPE)).toBe('follow-up')
+    expect(view.result.current.error).toBe(CHECK_THE_CHAT)
+  })
+})
+
+describe('a send in doubt behind one a Stop outran', () => {
+  it('is the one resent: the queue waits on it, not on the stamped one', async () => {
+    const later = {
+      ...createStructuredAgentSessionOutboxEntry({
+        clientMessageId: 'later',
+        sessionId: 'session-1',
+        text: 'later message',
+        attachments: [],
+        queuedAt: 2
+      }),
+      lastAttemptAt: 6,
+      state: 'unconfirmed' as const
+    }
+    seedAttempted({ stoppedBy: { operationId: 'stop-1' } })
+    writeOutbox('session-1', [...readOutbox('session-1'), later])
+    mount({ fence: 1, submissions: [], journalCursor: { epoch: 'e', sequence: 3 } })
+    await act(async () => {
+      await vi.advanceTimersByTimeAsync(60_000)
+    })
+    const sent = mocks.call.mock.calls.map((call) => call[2].envelope.clientOperationId)
+    expect(sent).toContain('later')
+    expect(sent).not.toContain('out')
+  })
+})
+
 describe('a message an older build held for a Retry', () => {
   it.each([
     ['outlived by a Stop', { outlivedStop: true, state: 'queued' }],
diff --git a/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.ts b/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.ts
index 66c40b1b48e..a445695f28b 100644
--- a/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.ts
+++ b/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.ts
@@ -137,8 +137,9 @@ export function useStructuredAgentSessionOutbox(args: {
   const [drains, setDrains] = useState(0)
   const drainAgain = useCallback(() => setDrains((count) => count + 1), [])
 
-  // Everything the journal settles, every time it moves: a row, a published card, the Stop's
-  // answer read through, or an entry an older build left waiting for a Retry.
+  // Everything the journal settles, every time it or the outbox moves: a row, a published card, the
+  // Stop's answer read through, or an entry an older build left. The outbox too, since an idle
+  // Stop answers at a cursor the journal already reached, and nothing else would move.
   useEffect(() => {
     const reading = {
       submissions,
@@ -189,7 +190,7 @@ export function useStructuredAgentSessionOutbox(args: {
       // Nothing above may have written the outbox, so the drain is told to look again.
       drainAgain()
     }
-  }, [drainAgain, journalCursor, queuedMessageIds, sessionId, submissions])
+  }, [drainAgain, journalCursor, outbox, queuedMessageIds, sessionId, submissions])
 
   const journalHasRow = useCallback(
     (clientMessageId: string) =>