diff --git a/src/renderer/src/components/native-chat/structured-agent-session-outbox-dispatch.ts b/src/renderer/src/components/native-chat/structured-agent-session-outbox-dispatch.ts
index 89d69cc6f5f..6f35a1e04fa 100644
--- a/src/renderer/src/components/native-chat/structured-agent-session-outbox-dispatch.ts
+++ b/src/renderer/src/components/native-chat/structured-agent-session-outbox-dispatch.ts
@@ -13,6 +13,7 @@ import {
 import {
   applyStructuredAgentSessionOutboxSettlement,
   settleStructuredAgentSessionSendAnswer,
+  structuredAgentSessionEntryOutlivedHostWindow,
   type StructuredAgentSessionSendAnswer,
   type StructuredAgentSessionOutboxSettlement,
   type StructuredAgentSessionSettledOutbox
@@ -279,7 +280,8 @@ export async function sendStructuredAgentSessionOutboxEntry(args: {
   const settlement = settleStructuredAgentSessionSendAnswer(answer, next.clientMessageId, {
     firstAttempt: onlyAttempt,
     answersProve,
-    journalHasRow: args.journalHasRow?.(next.clientMessageId) ?? false
+    journalHasRow: args.journalHasRow?.(next.clientMessageId) ?? false,
+    outlivedHostWindow: structuredAgentSessionEntryOutlivedHostWindow(next, Date.now())
   })
   settle(settlement)
   return settlement
diff --git a/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.offline-journal.test.tsx b/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.offline-journal.test.tsx
index d80302620a3..fdfcf7bab9e 100644
--- a/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.offline-journal.test.tsx
+++ b/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.offline-journal.test.tsx
@@ -21,6 +21,7 @@ vi.mock('@/runtime/structured-agent-session-client', () => ({
 vi.mock('sonner', () => ({ toast: { error: vi.fn() } }))
 
 import { createBrowserUuid } from '@/lib/browser-uuid'
+import { RuntimeRpcCallError } from '@/runtime/runtime-rpc-result'
 import { useStructuredAgentSessionOutbox } from './use-structured-agent-session-outbox'
 import { useStructuredAgentSessionConversationStop } from './use-structured-agent-session-conversation-stop'
 import type {
@@ -149,4 +150,46 @@ describe('while the journal is not live', () => {
       "Orca couldn't confirm your message reached the agent. Check the chat, then send it again if needed."
     )
   })
+
+  // A host that refuses before looking the id up refuses it every time: past its window that
+  // answer settles nothing, so the message comes back to be checked instead of blocking the queue.
+  it('a message past the window the host keeps refusing comes back after the next attempt', async () => {
+    seedSent('host refuses', Date.now() - AGENT_SESSION_MAX_OPERATION_REPLAY_AGE_MS - 60_000)
+    // As the client receives a refusal the host threw: an RPC error carrying it.
+    mocks.call.mockImplementation(async () => {
+      throw new RuntimeRpcCallError({
+        id: 'rpc-1',
+        ok: false,
+        error: {
+          code: 'runtime_error',
+          message: 'structured_agent_session_unsupported',
+          data: {
+            refusal: {
+              code: 'structured_agent_session_unsupported',
+              details: { reason: 'hostDisabled' }
+            }
+          }
+        }
+      })
+    })
+    mountChat(asWriteAs(async () => LOST))
+
+    await vi.waitFor(() => expect(readNativeChatDraftCache(SCOPE)).toBe('host refuses'), {
+      timeout: 3000
+    })
+    expect(mocks.call).toHaveBeenCalledOnce()
+    expect(readOutbox('session-1')).toEqual([])
+  })
+
+  it('a message past the window that only meets a lost connection keeps being sent', async () => {
+    seedSent('no contact', Date.now() - AGENT_SESSION_MAX_OPERATION_REPLAY_AGE_MS - 60_000)
+    mocks.call.mockRejectedValue(new Error('socket closed'))
+    mountChat(asWriteAs(async () => LOST))
+
+    await vi.waitFor(() => expect(mocks.call.mock.calls.length).toBeGreaterThanOrEqual(2), {
+      timeout: 5000
+    })
+    expect(readOutbox('session-1')).toHaveLength(1)
+    expect(readNativeChatDraftCache(SCOPE)).toBe('')
+  }, 10000)
 })
diff --git a/src/shared/structured-agent-session-draft-hand-off.test.ts b/src/shared/structured-agent-session-draft-hand-off.test.ts
index 0058a80f4b0..304f8b93270 100644
--- a/src/shared/structured-agent-session-draft-hand-off.test.ts
+++ b/src/shared/structured-agent-session-draft-hand-off.test.ts
@@ -63,7 +63,7 @@ describe('a queued draft handed off under a fresh submission id', () => {
           }
         },
         'draft',
-        { firstAttempt: false, answersProve: true, journalHasRow: false }
+        { firstAttempt: false, answersProve: true, journalHasRow: false, outlivedHostWindow: false }
       )
     ).toEqual({ kind: 'recorded' })
   })
diff --git a/src/shared/structured-agent-session-outbox-settlement.test.ts b/src/shared/structured-agent-session-outbox-settlement.test.ts
index e8abc6cc996..06e3be725d5 100644
--- a/src/shared/structured-agent-session-outbox-settlement.test.ts
+++ b/src/shared/structured-agent-session-outbox-settlement.test.ts
@@ -90,7 +90,8 @@ function refused(
 const FIRST: StructuredAgentSessionOutboxSettlementContext = {
   firstAttempt: true,
   answersProve: true,
-  journalHasRow: false
+  journalHasRow: false,
+  outlivedHostWindow: false
 }
 const RESEND_PROVING: StructuredAgentSessionOutboxSettlementContext = {
   ...FIRST,
@@ -617,6 +618,48 @@ describe('applying a settlement', () => {
   })
 })
 
+describe("past the host's window, a host answer that settles nothing", () => {
+  const PAST = { ...RESEND_OLD_HOST, outlivedHostWindow: true }
+  const hostAnswers: [string, StructuredAgentSessionSendAnswer][] = [
+    ['a refusal it returned', refused('agent_session_journal_unreadable')],
+    [
+      'a refusal it threw',
+      {
+        kind: 'thrown',
+        refusal: { kind: 'refused', code: 'structured_agent_session_unsupported' },
+        rpcCode: undefined
+      }
+    ],
+    ['a call it turned away', { kind: 'thrown', refusal: undefined, rpcCode: 'method_not_found' }]
+  ]
+
+  it.each(hostAnswers)(
+    '%s: comes back to check the chat, or is the row it shows',
+    (_label, answer) => {
+      expect(settleStructuredAgentSessionSendAnswer(answer, ID, RESEND_OLD_HOST).kind).toBe(
+        'unanswered'
+      )
+      expect(settleStructuredAgentSessionSendAnswer(answer, ID, PAST)).toEqual({
+        kind: 'returned',
+        words: ['sendOutcomeLost']
+      })
+      expect(
+        settleStructuredAgentSessionSendAnswer(answer, ID, { ...PAST, journalHasRow: true })
+      ).toEqual({ kind: 'recorded' })
+    }
+  )
+
+  it('but a lost connection is no answer from the host, so it still goes again', () => {
+    expect(
+      settleStructuredAgentSessionSendAnswer(
+        { kind: 'thrown', refusal: undefined, rpcCode: 'runtime_timeout' },
+        ID,
+        PAST
+      )
+    ).toEqual({ kind: 'unanswered' })
+  })
+})
+
 describe('the host window bounds every entry', () => {
   const pastWindow = MADE_AT + AGENT_SESSION_MAX_OPERATION_REPLAY_AGE_MS + 1
   const reading = {
diff --git a/src/shared/structured-agent-session-outbox-settlement.ts b/src/shared/structured-agent-session-outbox-settlement.ts
index da2f43c237f..8ff77776c98 100644
--- a/src/shared/structured-agent-session-outbox-settlement.ts
+++ b/src/shared/structured-agent-session-outbox-settlement.ts
@@ -57,6 +57,9 @@ export type StructuredAgentSessionOutboxSettlementContext = {
   answersProve: boolean
   /** The loaded journal holds a row for this id. */
   journalHasRow: boolean
+  /** The host's window for this id has closed, by the id's own time
+   *  (`structuredAgentSessionEntryOutlivedHostWindow`). */
+  outlivedHostWindow: boolean
 }
 
 /** Words for a message Orca can no longer settle with the host: an earlier attempt may already be
@@ -135,10 +138,34 @@ function thrownSettlement(
 }
 
 /** The host's answer to one attempt, as one of the three ends. */
+/** Whether the host itself answered: a refusal it returned or threw, or a code it turned the call
+ *  away with. Anything else is the transport, which says nothing about the host. */
+function answeredByHost(answer: StructuredAgentSessionSendAnswer): boolean {
+  return (
+    answer.kind === 'result' ||
+    answer.refusal !== undefined ||
+    agentSessionRpcErrorFailure(answer.rpcCode).kind === 'refused'
+  )
+}
+
+/** The host's answer to one attempt, as one of the three ends. Past the host's window for the id,
+ *  an answer the host gave that settles nothing never will (a host that refuses before looking the
+ *  id up refuses it every time), so the journal decides; lost contact still only goes again. */
 export function settleStructuredAgentSessionSendAnswer(
   answer: StructuredAgentSessionSendAnswer,
   clientMessageId: string,
   context: StructuredAgentSessionOutboxSettlementContext
+): StructuredAgentSessionOutboxSettlement {
+  const settlement = settleAnswer(answer, clientMessageId, context)
+  return settlement.kind === 'unanswered' && context.outlivedHostWindow && answeredByHost(answer)
+    ? settledByJournal(context)
+    : settlement
+}
+
+function settleAnswer(
+  answer: StructuredAgentSessionSendAnswer,
+  clientMessageId: string,
+  context: StructuredAgentSessionOutboxSettlementContext
 ): StructuredAgentSessionOutboxSettlement {
   if (answer.kind === 'thrown') {
     return thrownSettlement(answer, context)
@@ -177,8 +204,9 @@ export function structuredAgentSessionEntryHostWindowEndsAt(
   return madeAt === null ? null : madeAt + AGENT_SESSION_MAX_OPERATION_REPLAY_AGE_MS
 }
 
-/** Whether the host can no longer settle this id, so a host that keeps failing the request, or an
- *  answer that never comes, can't hold the entry forever. */
+/** Whether the host can no longer settle this id. Past it, a host answer that settles nothing
+ *  hands the entry back for the journal to decide, and a live journal settles one only an owed
+ *  answer would; lost contact alone keeps it, since it says nothing about the host. */
 export function structuredAgentSessionEntryOutlivedHostWindow(
   entry: Pick<StructuredAgentSessionOutboxEntry, 'clientMessageId'>,
   now: number
diff --git a/src/shared/structured-agent-session-outbox.queue-delivery.test.ts b/src/shared/structured-agent-session-outbox.queue-delivery.test.ts
index 18dcade0de3..a347f8c443a 100644
--- a/src/shared/structured-agent-session-outbox.queue-delivery.test.ts
+++ b/src/shared/structured-agent-session-outbox.queue-delivery.test.ts
@@ -147,7 +147,7 @@ describe('outbox queue delivery', () => {
         }
       },
       'client-1',
-      { firstAttempt: true, answersProve: false, journalHasRow: false }
+      { firstAttempt: true, answersProve: false, journalHasRow: false, outlivedHostWindow: false }
     )
     const stopped = stopStructuredAgentSessionOutbox([staged], [], 'client-1', 'stop-1').entries
     for (const entries of [stopped, [staged]]) {