diff --git a/config/reliability-gates.jsonc b/config/reliability-gates.jsonc
index e5d8b5b2c57..642918a992c 100644
--- a/config/reliability-gates.jsonc
+++ b/config/reliability-gates.jsonc
@@ -948,7 +948,7 @@
       "invariant": "One structured-send operation id causes at most one provider dispatch. A recorded or transport-ambiguous send reuses that id across retry, caller reconnect, client remount, and journal recovery; only a terminal rejection may rotate to a first delivery.",
       "oracle": "Inject adapter acknowledgement loss, RPC response loss, caller replacement, logical-client close after response, auth recovery with a written request, missing journal submissions, legacy pending rows, stale fences, operation expiry, mobile remount, and durable-journal capacity. Assert one provider dispatch or one operation id for every ambiguous retry, fresh identity only after rejection, and no eviction of ambiguous mobile ids.",
       "commands": [
-        "ORCA_BACKGROUND_LAUNCH=1 pnpm test src/shared/agent-session-operation-ledger.test.ts src/shared/structured-agent-session-send-disposition.test.ts src/main/runtime/agent-session-operation-admission.test.ts src/main/native-chat/agent-session-wire/structured-agent-session-refusal-retry.test.ts src/main/native-chat/agent-session-wire/structured-agent-session-send.test.ts src/main/runtime/orchestration/structured-mailbox-pointer-delivery.test.ts src/main/runtime/orchestration/structured-mailbox-pointer-host.test.ts src/main/runtime/orchestration/structured-pointer-operation-id.test.ts src/renderer/src/components/native-chat/use-structured-agent-session-outbox.test.tsx src/renderer/src/components/native-chat/use-structured-agent-session.test.tsx src/renderer/src/components/native-chat/NativeChatStructuredSessionDelivery.test.tsx src/renderer/src/lib/launch-structured-agent-session.test.ts",
+        "ORCA_BACKGROUND_LAUNCH=1 pnpm test src/shared/agent-session-operation-ledger.test.ts src/shared/structured-agent-session-send-disposition.test.ts src/main/runtime/agent-session-operation-admission.test.ts src/main/native-chat/agent-session-wire/structured-agent-session-refusal-retry.test.ts src/main/native-chat/agent-session-wire/structured-agent-session-send.test.ts src/main/runtime/orchestration/structured-mailbox-pointer-delivery.test.ts src/main/runtime/orchestration/structured-mailbox-pointer-host.test.ts src/main/runtime/orchestration/structured-pointer-operation-id.test.ts src/renderer/src/components/native-chat/use-structured-agent-session-outbox.test.tsx src/renderer/src/components/native-chat/use-structured-agent-session.test.tsx src/renderer/src/components/native-chat/NativeChatStructuredSessionDelivery.test.tsx src/renderer/src/components/native-chat/NativeChatStructuredSessionDelivery.probe.test.tsx src/renderer/src/lib/launch-structured-agent-session.test.ts",
         "ORCA_BACKGROUND_LAUNCH=1 pnpm --dir mobile test ../mobile/src/session/mobile-native-chat-image-attachment.test.ts ../mobile/src/session/use-mobile-native-chat-image-attachments.test.ts ../mobile/src/session/mobile-structured-send-operation-journal.test.ts ../mobile/src/session/mobile-structured-send-delivery.test.ts ../mobile/src/session/use-mobile-structured-agent-session-send.test.tsx ../mobile/src/session/use-mobile-structured-agent-session.test.tsx ../mobile/src/transport/mobile-relay-rpc-session.test.ts ../mobile/src/transport/rpc-client-delivery-ambiguity.test.ts ../mobile/src/transport/stable-logical-rpc-client.test.ts"
       ],
       "testFiles": [
@@ -963,6 +963,7 @@
         "src/renderer/src/components/native-chat/use-structured-agent-session-outbox.test.tsx",
         "src/renderer/src/components/native-chat/use-structured-agent-session.test.tsx",
         "src/renderer/src/components/native-chat/NativeChatStructuredSessionDelivery.test.tsx",
+        "src/renderer/src/components/native-chat/NativeChatStructuredSessionDelivery.probe.test.tsx",
         "src/renderer/src/lib/launch-structured-agent-session.test.ts",
         "mobile/src/session/mobile-native-chat-image-attachment.test.ts",
         "mobile/src/session/use-mobile-native-chat-image-attachments.test.ts",
@@ -1033,13 +1034,13 @@
       ],
       "evidenceRuns": [
         {
-          "date": "2026-09-12",
+          "date": "2026-10-04",
           "runner": "local",
           "platform": "macos",
-          "command": "ORCA_BACKGROUND_LAUNCH=1 pnpm test src/shared/agent-session-operation-ledger.test.ts src/shared/structured-agent-session-send-disposition.test.ts src/main/runtime/agent-session-operation-admission.test.ts src/main/native-chat/agent-session-wire/structured-agent-session-refusal-retry.test.ts src/main/native-chat/agent-session-wire/structured-agent-session-send.test.ts src/main/runtime/orchestration/structured-mailbox-pointer-delivery.test.ts src/main/runtime/orchestration/structured-mailbox-pointer-host.test.ts src/main/runtime/orchestration/structured-pointer-operation-id.test.ts src/renderer/src/components/native-chat/use-structured-agent-session-outbox.test.tsx src/renderer/src/components/native-chat/use-structured-agent-session.test.tsx src/renderer/src/components/native-chat/NativeChatStructuredSessionDelivery.test.tsx src/renderer/src/lib/launch-structured-agent-session.test.ts",
+          "command": "ORCA_BACKGROUND_LAUNCH=1 pnpm test src/shared/agent-session-operation-ledger.test.ts src/shared/structured-agent-session-send-disposition.test.ts src/main/runtime/agent-session-operation-admission.test.ts src/main/native-chat/agent-session-wire/structured-agent-session-refusal-retry.test.ts src/main/native-chat/agent-session-wire/structured-agent-session-send.test.ts src/main/runtime/orchestration/structured-mailbox-pointer-delivery.test.ts src/main/runtime/orchestration/structured-mailbox-pointer-host.test.ts src/main/runtime/orchestration/structured-pointer-operation-id.test.ts src/renderer/src/components/native-chat/use-structured-agent-session-outbox.test.tsx src/renderer/src/components/native-chat/use-structured-agent-session.test.tsx src/renderer/src/components/native-chat/NativeChatStructuredSessionDelivery.test.tsx src/renderer/src/components/native-chat/NativeChatStructuredSessionDelivery.probe.test.tsx src/renderer/src/lib/launch-structured-agent-session.test.ts",
           "result": "passed",
-          "durationSeconds": 22.1,
-          "summary": "Thirteen focused host, shared, renderer, and orchestration files passed 148 tests."
+          "durationSeconds": 42.3,
+          "summary": "Thirteen focused host, shared, renderer, and orchestration files passed 197 tests after the delivery probe tests moved to their own file."
         },
         {
           "date": "2026-09-12",
diff --git a/src/renderer/src/components/native-chat/NativeChatMessageRow.test.tsx b/src/renderer/src/components/native-chat/NativeChatMessageRow.test.tsx
index bcecab05bc6..f9e247d1354 100644
--- a/src/renderer/src/components/native-chat/NativeChatMessageRow.test.tsx
+++ b/src/renderer/src/components/native-chat/NativeChatMessageRow.test.tsx
@@ -3,7 +3,7 @@ import '@testing-library/jest-dom/vitest'
 import { cleanup, fireEvent, render, screen, waitFor } from '@testing-library/react'
 import { afterEach, describe, expect, it, vi } from 'vitest'
 import type { NativeChatMessage } from '../../../../shared/native-chat-types'
-import { MessageRow } from './NativeChatMessageRow'
+import { MessageRow, type NativeChatDeliveryNotice } from './NativeChatMessageRow'
 
 afterEach(cleanup)
 
@@ -163,8 +163,8 @@ describe('MessageRow send mode', () => {
   })
 })
 
-describe('a user message that did not go through', () => {
-  function renderUser(deliveryNotice?: { text: string; onRetry?: () => void }) {
+describe('what a user message says about its delivery', () => {
+  function renderUser(deliveryNotice?: NativeChatDeliveryNotice) {
     return render(
       <MessageRow
         message={{
@@ -203,4 +203,41 @@ describe('a user message that did not go through', () => {
     renderUser()
     expect(screen.queryByRole('button', { name: 'Retry' })).toBeNull()
   })
+
+  // Muted, in the time's place, and shown without hover: a message nothing confirmed yet never
+  // looks like one that went through. Copy keeps its hover reveal, and the row its height.
+  it('says quietly that it is still sending in place of its time, with no Retry', () => {
+    renderUser({ sending: true })
+
+    const sending = screen.getByText('Sending…')
+    const copy = screen.getByRole('button', { name: 'Copy message' })
+    expect(sending).toHaveClass('text-xs', 'text-muted-foreground')
+    expect(Array.from(sending.parentElement!.children)).toEqual([copy, sending])
+    expect(sending.parentElement).not.toHaveClass('can-hover:opacity-0')
+    expect(sending.parentElement!.parentElement).toHaveClass('group')
+    expect(copy).toHaveClass('can-hover:opacity-0', 'group-hover:opacity-100')
+    expect(screen.queryByRole('time')).toBeNull()
+    expect(screen.queryByRole('button', { name: 'Retry' })).toBeNull()
+  })
+
+  it('keeps the same row when the message is confirmed, with the time back in its place', () => {
+    const { rerender } = renderUser({ sending: true })
+    const meta = screen.getByText('Sending…').parentElement
+    rerender(
+      <MessageRow
+        message={{
+          id: 'message',
+          role: 'user',
+          timestamp: 0,
+          source: 'transcript',
+          blocks: [{ type: 'text', text: 'Message text' }]
+        }}
+        expandSignal={false}
+        onScrollMessageToTop={vi.fn()}
+      />
+    )
+    expect(screen.queryByText('Sending…')).toBeNull()
+    expect(screen.getByRole('time').parentElement).toBe(meta)
+    expect(meta).toHaveClass('can-hover:opacity-0')
+  })
 })
diff --git a/src/renderer/src/components/native-chat/NativeChatMessageRow.tsx b/src/renderer/src/components/native-chat/NativeChatMessageRow.tsx
index 234934664f4..10c8a68de07 100644
--- a/src/renderer/src/components/native-chat/NativeChatMessageRow.tsx
+++ b/src/renderer/src/components/native-chat/NativeChatMessageRow.tsx
@@ -28,12 +28,45 @@ import type {
 } from './native-chat-subagent-sections'
 import type { RuntimeFileOperationArgs } from '@/runtime/runtime-file-client'
 
-/** What a user message says under it when it did not go through, with its own Retry when the
- *  surface can send it again. */
-export type NativeChatDeliveryNotice = {
-  text: string
-  onRetry?: () => void
-  onDismiss?: () => void
+/** What a user message says about its delivery: that nothing has confirmed it yet, quietly in
+ *  place of its time, or that it did not go through, with its own Retry when the surface can send
+ *  it again. */
+export type NativeChatDeliveryNotice =
+  | { sending: true; text?: never; onRetry?: never; onDismiss?: never }
+  | { sending?: never; text: string; onRetry?: () => void; onDismiss?: () => void }
+
+const USER_META_REVEAL =
+  'transition-opacity can-hover:pointer-events-none can-hover:opacity-0 group-hover:pointer-events-auto group-hover:opacity-100 [.group:has(:focus-visible)_&]:pointer-events-auto [.group:has(:focus-visible)_&]:opacity-100'
+
+/** Under a user message: copy + timestamp, revealed together like the agent controls row. Until
+ *  confirmed, a quiet "Sending…" stays visible in the time's place and copy keeps its own reveal,
+ *  so the row keeps its height when it clears. Image-only prompts have no text to copy. */
+function UserMessageMeta({
+  markdown,
+  timestamp,
+  sending
+}: {
+  markdown: string
+  timestamp: number | null
+  sending: boolean
+}): React.JSX.Element | null {
+  if (!markdown && timestamp === null && !sending) {
+    return null
+  }
+  return (
+    <div className={cn('flex select-none items-center gap-1', !sending && USER_META_REVEAL)}>
+      {markdown ? (
+        <NativeChatCopyButton text={markdown} className={sending ? USER_META_REVEAL : undefined} />
+      ) : null}
+      {sending ? (
+        <span className="text-xs whitespace-nowrap text-muted-foreground">
+          {translate('components.native-chat.messageSending', 'Sending…')}
+        </span>
+      ) : (
+        <NativeChatMessageTimestamp timestamp={timestamp} focusable />
+      )}
+    </div>
+  )
 }
 
 /** One message: its prose first, then a collapsible run folding all of the
@@ -178,15 +211,12 @@ export const MessageRow = memo(function MessageRow({
             <span>{translate('components.native-chat.goal.sentAsGoal', 'Sent as goal')}</span>
           </div>
         ) : null}
-        {/* Copy + timestamp reveal together, mirroring the agent controls row.
-            Image-only prompts have no text to copy, so the button is omitted. */}
-        {markdown || message.timestamp !== null ? (
-          <div className="flex select-none items-center gap-1 transition-opacity can-hover:pointer-events-none can-hover:opacity-0 group-hover:pointer-events-auto group-hover:opacity-100 [.group:has(:focus-visible)_&]:pointer-events-auto [.group:has(:focus-visible)_&]:opacity-100">
-            {markdown ? <NativeChatCopyButton text={markdown} /> : null}
-            <NativeChatMessageTimestamp timestamp={message.timestamp} focusable />
-          </div>
-        ) : null}
-        {deliveryNotice ? (
+        <UserMessageMeta
+          markdown={markdown}
+          timestamp={message.timestamp}
+          sending={deliveryNotice?.sending === true}
+        />
+        {deliveryNotice?.text !== undefined ? (
           <div className="flex max-w-[85%] items-center gap-2 text-[11px] text-destructive/80">
             <span className="min-w-0 break-words">{deliveryNotice.text}</span>
             {deliveryNotice.onDismiss ? (
diff --git a/src/renderer/src/components/native-chat/NativeChatStructuredSession.test-harness.tsx b/src/renderer/src/components/native-chat/NativeChatStructuredSession.test-harness.tsx
index ee876868c35..89fda3f7f31 100644
--- a/src/renderer/src/components/native-chat/NativeChatStructuredSession.test-harness.tsx
+++ b/src/renderer/src/components/native-chat/NativeChatStructuredSession.test-harness.tsx
@@ -1,3 +1,4 @@
+import { act } from '@testing-library/react'
 import { forwardRef, useImperativeHandle, useRef } from 'react'
 import { vi } from 'vitest'
 import type { AgentJournalRenderItem } from '../../../../shared/agent-session-journal-types'
@@ -27,7 +28,8 @@ function absent<T>(): T | undefined {
   return undefined
 }
 
-/** Stands in for the transcript: renders only each message's delivery notice and its Retry. */
+/** Stands in for the transcript: renders only each message's delivery notice and its Retry, or the
+ *  row's quiet "Sending…" while nothing has confirmed it. */
 export function DeliveryNoticesMock({
   notices
 }: {
@@ -37,7 +39,7 @@ export function DeliveryNoticesMock({
     <div data-testid="message-list">
       {[...(notices ?? [])].map(([id, notice]) => (
         <div key={id} data-message-id={id}>
-          <span>{notice.text}</span>
+          <span>{notice.sending ? 'Sending…' : notice.text}</span>
           {notice.onRetry ? (
             <button type="button" onClick={notice.onRetry}>
               Retry
@@ -49,6 +51,43 @@ export function DeliveryNoticesMock({
   )
 }
 
+export function useProbeClock(): void {
+  vi.useFakeTimers({ toFake: ['setTimeout', 'clearTimeout', 'Date'] })
+}
+
+export async function advanceProbeClock(milliseconds: number): Promise<void> {
+  await act(async () => {
+    await vi.advanceTimersByTimeAsync(milliseconds)
+  })
+}
+
+export function seededEntry(
+  sessionId: string,
+  clientMessageId: string,
+  text: string,
+  state: 'queued' | 'unconfirmed'
+) {
+  return {
+    clientMessageId,
+    sessionId,
+    body: { kind: 'message', role: 'user', blocks: [{ type: 'text', text }] },
+    previewUris: [],
+    state,
+    queuedAt: clientMessageId === 'op-head' ? 1 : 2,
+    lastAttemptAt: null,
+    // Already force-retried once, so the automatic probe leaves the head alone
+    // and only the user's Retry moves it.
+    retryAfterUnknownSubmittedAt: -1
+  }
+}
+
+export function seedOutbox(sessionId: string, entries: unknown[]): void {
+  localStorage.setItem(
+    `orca:desktopStructuredAgentSessionOutbox:v1:${encodeURIComponent(sessionId)}`,
+    JSON.stringify(entries)
+  )
+}
+
 type StructuredSessionMessageListProps = {
   allowFileUriLinks?: boolean
   isVisible?: boolean
diff --git a/src/renderer/src/components/native-chat/NativeChatStructuredSessionDelivery.probe.test.tsx b/src/renderer/src/components/native-chat/NativeChatStructuredSessionDelivery.probe.test.tsx
new file mode 100644
index 00000000000..4a89074d23f
--- /dev/null
+++ b/src/renderer/src/components/native-chat/NativeChatStructuredSessionDelivery.probe.test.tsx
@@ -0,0 +1,362 @@
+// The automatic probe of an unconfirmed outbox head: when it resends under the same
+// operation id, and when it parks the entry for the user's Retry instead.
+
+// @vitest-environment happy-dom
+
+import { act, cleanup, render, screen } from '@testing-library/react'
+import React from 'react'
+import { afterEach, describe, expect, it, vi } from 'vitest'
+
+const { mocks, moduleFactories, resetStructuredSessionMocks } = await vi.hoisted(async () =>
+  (await import('./NativeChatStructuredSession.test-harness')).createStructuredSessionMocks()
+)
+
+vi.mock('@/runtime/structured-agent-session-client', () =>
+  moduleFactories.structuredAgentSessionClient()
+)
+vi.mock('./use-structured-agent-session', () => moduleFactories.useStructuredAgentSession())
+vi.mock('./use-native-chat-font-scale', () => moduleFactories.useNativeChatFontScale())
+vi.mock('./use-native-chat-file-link-context', () => moduleFactories.useNativeChatFileLinkContext())
+vi.mock('./use-native-chat-file-link-click', () => moduleFactories.useNativeChatFileLinkClick())
+vi.mock('./NativeChatMessageList', () => moduleFactories.nativeChatMessageList())
+vi.mock('./NativeChatComposer', () => moduleFactories.nativeChatComposer())
+vi.mock('./NativeChatEmptyState', () => moduleFactories.nativeChatEmptyState())
+vi.mock('./NativeChatApprovalCard', () => moduleFactories.nativeChatApprovalCard())
+vi.mock('./NativeChatQuestionCard', () => moduleFactories.nativeChatQuestionCard())
+
+import { NativeChatStructuredSession } from './NativeChatStructuredSession'
+import {
+  advanceProbeClock,
+  seededEntry,
+  seedOutbox,
+  useProbeClock
+} from './NativeChatStructuredSession.test-harness'
+
+describe('NativeChatStructuredSession delivery probe', () => {
+  afterEach(() => {
+    cleanup()
+    vi.useRealTimers()
+    localStorage.clear()
+    resetStructuredSessionMocks()
+  })
+
+  it('resends a transport-unconfirmed head so later messages are not wedged', async () => {
+    useProbeClock()
+    mocks.mode = 'outbox'
+    mocks.submissions = []
+    mocks.call.mockRejectedValueOnce(new Error('socket closed')).mockResolvedValue({
+      ok: true,
+      value: { submission: { clientMessageId: 'client-1', dispatchState: 'accepted' } }
+    })
+
+    render(
+      <NativeChatStructuredSession
+        isVisible
+        isFocusedGroup
+        tabId="structured-tab-wedge"
+        sessionId="session-wedge"
+        target={{ kind: 'local' }}
+        agent="codex"
+      />
+    )
+
+    const send = mocks.composerProps?.structuredTransport?.send as
+      | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
+      | undefined
+    await act(async () => {
+      expect(send?.('first', [])).toBe(true)
+    })
+    expect(mocks.call).toHaveBeenCalledOnce()
+
+    await act(async () => {
+      expect(send?.('second', [])).toBe(true)
+    })
+    await advanceProbeClock(999)
+    expect(mocks.call).toHaveBeenCalledOnce()
+    await advanceProbeClock(1)
+    // The head is probed automatically, clears, and the queue drains.
+    expect(mocks.call).toHaveBeenCalledTimes(3)
+    expect(screen.queryByText('Message delivery is unconfirmed.')).toBeNull()
+  }, 20000)
+
+  it('probes the same operation without marking an explicit user retry', async () => {
+    useProbeClock()
+    mocks.mode = 'outbox'
+    mocks.submissions = []
+    mocks.call.mockRejectedValueOnce(new Error('socket closed')).mockResolvedValue({
+      ok: true,
+      value: { submission: { clientMessageId: 'client-1', dispatchState: 'accepted' } }
+    })
+
+    render(
+      <NativeChatStructuredSession
+        isVisible
+        isFocusedGroup
+        tabId="structured-tab-probe-flag"
+        sessionId="session-probe-flag"
+        target={{ kind: 'local' }}
+        agent="codex"
+      />
+    )
+
+    const send = mocks.composerProps?.structuredTransport?.send as
+      | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
+      | undefined
+    await act(async () => {
+      expect(send?.('first', [])).toBe(true)
+    })
+    await advanceProbeClock(999)
+    expect(mocks.call).toHaveBeenCalledOnce()
+    await advanceProbeClock(1)
+    expect(mocks.call).toHaveBeenCalledTimes(2)
+
+    const first = mocks.call.mock.calls[0]?.[2] as Record<string, unknown>
+    const probe = mocks.call.mock.calls[1]?.[2] as Record<string, unknown>
+    expect(probe.retryUnknown).toBeUndefined()
+    // Same operation id: both dedupe layers key off it.
+    expect((probe.envelope as { clientOperationId: string }).clientOperationId).toBe(
+      (first.envelope as { clientOperationId: string }).clientOperationId
+    )
+  }, 20000)
+
+  it('parks a host-confirmed unknown instead of probing it', async () => {
+    useProbeClock()
+    mocks.mode = 'outbox'
+    mocks.call.mockRejectedValueOnce(new Error('socket closed')).mockResolvedValue({
+      ok: true,
+      value: { submission: { clientMessageId: 'client-1', dispatchState: 'accepted' } }
+    })
+
+    render(
+      <NativeChatStructuredSession
+        isVisible
+        isFocusedGroup
+        tabId="structured-tab-parked"
+        sessionId="session-parked"
+        target={{ kind: 'local' }}
+        agent="codex"
+      />
+    )
+
+    const send = mocks.composerProps?.structuredTransport?.send as
+      | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
+      | undefined
+    await act(async () => {
+      expect(send?.('first', [])).toBe(true)
+    })
+    expect(mocks.call).toHaveBeenCalledOnce()
+
+    const sent = mocks.call.mock.calls[0]?.[2] as { envelope: { clientOperationId: string } }
+    // The host now reports an unresolved unknown: another replay is the user's call.
+    mocks.submissions = [
+      {
+        clientMessageId: sent.envelope.clientOperationId,
+        fence: 1,
+        payloadFingerprint: 'fp',
+        dispatchState: 'unknown',
+        providerItemId: null,
+        reason: null,
+        submittedAt: 1,
+        resolvedAt: null
+      }
+    ]
+    // Queue a second message purely to re-render so the effect observes the
+    // new submissions; it must stay wedged behind the parked head.
+    await act(async () => {
+      send?.('second', [])
+    })
+    await advanceProbeClock(3000)
+    // From the row on, only the user's Retry moves it, so it says so.
+    expect(screen.getByText('Message delivery is unconfirmed.')).toBeTruthy()
+    expect(mocks.call).toHaveBeenCalledOnce()
+  }, 20000)
+
+  it('still probes while streaming batches rebuild the submissions array', async () => {
+    useProbeClock()
+    mocks.mode = 'outbox'
+    mocks.submissions = []
+    mocks.call.mockRejectedValueOnce(new Error('socket closed')).mockResolvedValue({
+      ok: true,
+      value: { submission: { clientMessageId: 'client-1', dispatchState: 'accepted' } }
+    })
+
+    const makeView = (): React.ReactElement => (
+      <NativeChatStructuredSession
+        isVisible
+        isFocusedGroup
+        tabId="structured-tab-churn"
+        sessionId="session-churn"
+        target={{ kind: 'local' }}
+        agent="codex"
+      />
+    )
+    const { rerender } = render(makeView())
+
+    const send = mocks.composerProps?.structuredTransport?.send as
+      | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
+      | undefined
+    await act(async () => {
+      expect(send?.('first', [])).toBe(true)
+    })
+    expect(mocks.call).toHaveBeenCalledOnce()
+
+    // Each batch mints a fresh submissions array for an unrelated message. An
+    // array-identity dependency restarts the backoff on every one of these, so a
+    // stream that outlasts the delay would never let the probe fire.
+    for (let index = 0; index < 12; index += 1) {
+      mocks.submissions = [
+        {
+          clientMessageId: `other-${index}`,
+          fence: 1,
+          payloadFingerprint: 'fp',
+          dispatchState: 'accepted',
+          providerItemId: null,
+          reason: null,
+          submittedAt: index,
+          resolvedAt: index
+        }
+      ]
+      await act(async () => {
+        rerender(makeView())
+        await vi.advanceTimersByTimeAsync(250)
+      })
+    }
+
+    // Asserted with no trailing grace period: the probe must have fired *during*
+    // the stream, not after it went quiet.
+    expect(mocks.call).toHaveBeenCalledTimes(2)
+  }, 20000)
+
+  it('restarts probe delay when the runtime target changes', async () => {
+    useProbeClock()
+    mocks.mode = 'outbox'
+    mocks.call.mockRejectedValueOnce(new Error('socket closed')).mockResolvedValue({
+      ok: true,
+      value: { submission: { clientMessageId: 'client-1', dispatchState: 'accepted' } }
+    })
+
+    const makeView = (
+      target: { kind: 'local' } | { kind: 'environment'; environmentId: string }
+    ) => (
+      <NativeChatStructuredSession
+        isVisible
+        isFocusedGroup
+        tabId="structured-tab-target-switch"
+        sessionId="session-target-switch"
+        target={target}
+        agent="codex"
+      />
+    )
+    const { rerender } = render(makeView({ kind: 'local' }))
+    const send = mocks.composerProps?.structuredTransport?.send as
+      | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
+      | undefined
+    await act(async () => {
+      expect(send?.('first', [])).toBe(true)
+    })
+    expect(mocks.call).toHaveBeenCalledOnce()
+
+    await advanceProbeClock(300)
+    rerender(makeView({ kind: 'environment', environmentId: 'env-1' }))
+    await advanceProbeClock(600)
+    expect(mocks.call).toHaveBeenCalledOnce()
+    await advanceProbeClock(399)
+    expect(mocks.call).toHaveBeenCalledOnce()
+    await advanceProbeClock(1)
+    expect(mocks.call).toHaveBeenCalledTimes(2)
+  }, 10000)
+
+  it('never auto-probes an entry the user already force-retried', async () => {
+    useProbeClock()
+    mocks.mode = 'outbox'
+    mocks.submissions = []
+    mocks.call.mockRejectedValue(new Error('socket closed'))
+    seedOutbox('session-forced', [seededEntry('session-forced', 'op-head', 'first', 'unconfirmed')])
+
+    render(
+      <NativeChatStructuredSession
+        isVisible
+        isFocusedGroup
+        tabId="structured-tab-forced"
+        sessionId="session-forced"
+        target={{ kind: 'local' }}
+        agent="codex"
+      />
+    )
+
+    await advanceProbeClock(3000)
+    // Only the user's Retry moves it, so it says so.
+    expect(screen.getByText('Message delivery is unconfirmed.')).toBeTruthy()
+    expect(mocks.call).not.toHaveBeenCalled()
+  }, 20000)
+
+  it('does not hot-loop when the host answers pending', async () => {
+    useProbeClock()
+    mocks.mode = 'outbox'
+    mocks.call.mockResolvedValue({
+      ok: true,
+      value: { submission: { clientMessageId: 'client-1', dispatchState: 'pending' } }
+    })
+
+    render(
+      <NativeChatStructuredSession
+        isVisible
+        isFocusedGroup
+        tabId="structured-tab-pending"
+        sessionId="session-pending"
+        target={{ kind: 'local' }}
+        agent="codex"
+      />
+    )
+
+    const send = mocks.composerProps?.structuredTransport?.send as
+      | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
+      | undefined
+    await act(async () => {
+      expect(send?.('first', [])).toBe(true)
+    })
+    expect(mocks.call).toHaveBeenCalledOnce()
+
+    // A host-pending entry stays parked until the journal answers it.
+    await advanceProbeClock(999)
+    expect(mocks.call).toHaveBeenCalledOnce()
+    await advanceProbeClock(1)
+    expect(mocks.call).toHaveBeenCalledOnce()
+    await advanceProbeClock(1500)
+    expect(mocks.call).toHaveBeenCalledOnce()
+  }, 20000)
+
+  it('keeps probing past the old five-attempt budget', async () => {
+    mocks.mode = 'outbox'
+    mocks.call.mockRejectedValue(new Error('socket closed'))
+    vi.useFakeTimers({ shouldAdvanceTime: true })
+    try {
+      render(
+        <NativeChatStructuredSession
+          isVisible
+          isFocusedGroup
+          tabId="structured-tab-budget"
+          sessionId="session-budget"
+          target={{ kind: 'local' }}
+          agent="codex"
+        />
+      )
+
+      const send = mocks.composerProps?.structuredTransport?.send as
+        | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
+        | undefined
+      expect(send?.('first', [])).toBe(true)
+
+      // Backoff is 1+2+4+8+16 = 31s for five probes, which was the old hard budget.
+      // Step past it; a seventh call proves the probe re-arms instead of giving up.
+      for (let step = 0; step < 12; step += 1) {
+        await act(async () => {
+          await vi.advanceTimersByTimeAsync(8_000)
+        })
+      }
+      expect(mocks.call.mock.calls.length).toBeGreaterThanOrEqual(7)
+    } finally {
+      vi.useRealTimers()
+    }
+  }, 30000)
+})
diff --git a/src/renderer/src/components/native-chat/NativeChatStructuredSessionDelivery.test.tsx b/src/renderer/src/components/native-chat/NativeChatStructuredSessionDelivery.test.tsx
index 64d47882740..d5493654e8e 100644
--- a/src/renderer/src/components/native-chat/NativeChatStructuredSessionDelivery.test.tsx
+++ b/src/renderer/src/components/native-chat/NativeChatStructuredSessionDelivery.test.tsx
@@ -1,5 +1,5 @@
 // The delivery notice and the outbox queue behind it: which entry a Retry acts
-// on, when no notice is owed at all, and how a host-confirmed unknown is probed.
+// on, and when no notice is owed at all. The automatic probe is in the .probe suite.
 
 // @vitest-environment happy-dom
 
@@ -187,20 +187,14 @@ vi.mock('./NativeChatQuestionCard', () => ({
 }))
 
 import { NativeChatStructuredSession } from './NativeChatStructuredSession'
-import { appendStructuredAgentSessionOutboxMessage } from './structured-agent-session-outbox-storage'
+import { seededEntry, seedOutbox } from './NativeChatStructuredSession.test-harness'
+import {
+  appendStructuredAgentSessionOutboxMessage,
+  getStructuredAgentSessionOutbox
+} from './structured-agent-session-outbox-storage'
 
 const REFUSED_RESTART = "The agent couldn't restart. Your message was not sent."
 
-function useProbeClock(): void {
-  vi.useFakeTimers({ toFake: ['setTimeout', 'clearTimeout', 'Date'] })
-}
-
-async function advanceProbeClock(milliseconds: number): Promise<void> {
-  await act(async () => {
-    await vi.advanceTimersByTimeAsync(milliseconds)
-  })
-}
-
 describe('NativeChatStructuredSession delivery', () => {
   afterEach(() => {
     cleanup()
@@ -222,43 +216,12 @@ describe('NativeChatStructuredSession delivery', () => {
     mocks.backgroundTasks = []
   })
 
-  function seededEntry(
-    sessionId: string,
-    clientMessageId: string,
-    text: string,
-    state: 'queued' | 'unconfirmed'
-  ) {
-    return {
-      clientMessageId,
-      sessionId,
-      body: { kind: 'message', role: 'user', blocks: [{ type: 'text', text }] },
-      previewUris: [],
-      state,
-      queuedAt: clientMessageId === 'op-head' ? 1 : 2,
-      lastAttemptAt: null,
-      // Already force-retried once, so the automatic probe leaves the head alone
-      // and only the user's Retry moves it.
-      retryAfterUnknownSubmittedAt: -1
-    }
-  }
-
-  function seedOutbox(sessionId: string, entries: unknown[]): void {
-    localStorage.setItem(
-      `orca:desktopStructuredAgentSessionOutbox:v1:${encodeURIComponent(sessionId)}`,
-      JSON.stringify(entries)
-    )
-  }
-
-  it('retries an unconfirmed transport send and clears the delivery notice', async () => {
+  // Resent under its own id until the host answers, so its row says only that it is still sending.
+  it('says a send whose answer was lost is sending until it confirms on its own, with no Retry', async () => {
     mocks.mode = 'outbox'
     mocks.call.mockRejectedValueOnce(new Error('socket closed')).mockResolvedValueOnce({
       ok: true,
-      value: {
-        submission: {
-          clientMessageId: 'client-1',
-          dispatchState: 'accepted'
-        }
-      }
+      value: { submission: { clientMessageId: 'client-1', dispatchState: 'accepted' } }
     })
 
     render(
@@ -276,14 +239,126 @@ describe('NativeChatStructuredSession delivery', () => {
       | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
       | undefined
     expect(send?.('hello', [])).toBe(true)
-    await waitFor(() => expect(mocks.call).toHaveBeenCalledOnce())
-    await waitFor(() => expect(screen.getByText('Message delivery is unconfirmed.')).toBeTruthy())
+    // From the moment it is sent, through the lost answer, until the host confirms it.
+    await waitFor(() => expect(screen.getByText('Sending…')).toBeTruthy())
+    await waitFor(() =>
+      expect(getStructuredAgentSessionOutbox('session-1')).toMatchObject([{ state: 'unconfirmed' }])
+    )
+    expect(screen.getByText('Sending…')).toBeTruthy()
+    expect(screen.queryByText('Message delivery is unconfirmed.')).toBeNull()
+    expect(screen.queryByRole('button', { name: /Retry/ })).toBeNull()
 
-    fireEvent.click(screen.getByRole('button', { name: /Retry/ }))
+    await waitFor(() => expect(mocks.call).toHaveBeenCalledTimes(2), { timeout: 5000 })
+    expect(mocks.call.mock.calls[1]?.[2]).toEqual(mocks.call.mock.calls[0]?.[2])
+    await waitFor(() => expect(screen.queryByText('Sending…')).toBeNull())
+    expect(getStructuredAgentSessionOutbox('session-1')).toEqual([])
+    expect(screen.queryByText('Message delivery is unconfirmed.')).toBeNull()
+  }, 10000)
 
-    await waitFor(() => expect(mocks.call).toHaveBeenCalledTimes(2))
-    await waitFor(() => expect(screen.queryByText('Message delivery is unconfirmed.')).toBeNull())
-  })
+  // Reopened mid-send, the send is read back in doubt; the probe resends it under its own id.
+  function seedMidSend(sessionId: string, patch: Record<string, unknown> = {}): void {
+    seedOutbox(sessionId, [
+      {
+        ...seededEntry(sessionId, 'op-sent', 'first', 'queued'),
+        state: 'dispatching',
+        lastAttemptAt: 1,
+        retryAfterUnknownSubmittedAt: null,
+        ...patch
+      }
+    ])
+  }
+
+  function renderSession(sessionId: string): void {
+    render(
+      <NativeChatStructuredSession
+        isVisible
+        isFocusedGroup
+        tabId={`structured-tab-${sessionId}`}
+        sessionId={sessionId}
+        target={{ kind: 'local' }}
+        agent="codex"
+      />
+    )
+  }
+
+  it('says a send reopened mid-send is sending while it is resent, until it settles', async () => {
+    mocks.mode = 'outbox'
+    mocks.submissions = []
+    mocks.call.mockResolvedValue({
+      ok: true,
+      value: { submission: { clientMessageId: 'op-sent', dispatchState: 'accepted' } }
+    })
+    seedMidSend('session-reopened')
+
+    renderSession('session-reopened')
+
+    expect(getStructuredAgentSessionOutbox('session-reopened')).toMatchObject([
+      { clientMessageId: 'op-sent', state: 'unconfirmed' }
+    ])
+    expect(screen.getByText('Sending…')).toBeTruthy()
+    expect(screen.queryByText('Message delivery is unconfirmed.')).toBeNull()
+    expect(screen.queryByRole('button', { name: /Retry/ })).toBeNull()
+    await waitFor(() => expect(mocks.call).toHaveBeenCalledOnce(), { timeout: 3000 })
+    expect(mocks.call.mock.calls[0]?.[2]).toMatchObject({
+      envelope: { clientOperationId: 'op-sent' }
+    })
+    await waitFor(() => expect(getStructuredAgentSessionOutbox('session-reopened')).toEqual([]))
+    expect(screen.queryByText('Sending…')).toBeNull()
+    expect(screen.queryByText('Message delivery is unconfirmed.')).toBeNull()
+  }, 10000)
+
+  it.each([
+    ['a live unknown', {}],
+    ['a recovered unknown', { recovered: true }],
+    ["an older host's recovered unknown", { reason: 'host_restarted_before_acknowledgement' }]
+  ])(
+    'says a send reopened mid-send is unconfirmed, with its Retry, once the journal holds %s',
+    async (label, patch) => {
+      mocks.mode = 'outbox'
+      const sessionId = `session-reopened-${label.replace(/\W+/g, '-')}`
+      mocks.submissions = [
+        {
+          clientMessageId: 'op-sent',
+          fence: 1,
+          payloadFingerprint: 'fp',
+          dispatchState: 'unknown',
+          providerItemId: null,
+          reason: null,
+          submittedAt: 1,
+          resolvedAt: null,
+          ...patch
+        }
+      ]
+      seedMidSend(sessionId)
+
+      renderSession(sessionId)
+
+      await waitFor(() => expect(screen.getByText('Message delivery is unconfirmed.')).toBeTruthy())
+      expect(screen.getByRole('button', { name: /Retry/ })).toBeTruthy()
+      expect(screen.queryByText('Sending…')).toBeNull()
+      await act(async () => {
+        await new Promise((resolve) => setTimeout(resolve, 1500))
+      })
+      expect(mocks.call).not.toHaveBeenCalled()
+    },
+    10000
+  )
+
+  it('says a send a Stop outlived is unconfirmed when reopened, as nothing resends it', async () => {
+    mocks.mode = 'outbox'
+    mocks.submissions = []
+    seedMidSend('session-reopened-stopped', { outlivedStop: true })
+
+    renderSession('session-reopened-stopped')
+
+    expect(screen.getByText('Message delivery is unconfirmed.')).toBeTruthy()
+    expect(screen.getByRole('button', { name: /Retry/ })).toBeTruthy()
+    expect(screen.queryByText('Sending…')).toBeNull()
+    await act(async () => {
+      await new Promise((resolve) => setTimeout(resolve, 1500))
+    })
+    expect(mocks.call).not.toHaveBeenCalled()
+  }, 10000)
 
   it('retries the head, not a later stuck message', async () => {
     mocks.mode = 'outbox'
@@ -498,343 +573,6 @@ describe('NativeChatStructuredSession delivery', () => {
     })
   })
 
-  it('resends a transport-unconfirmed head so later messages are not wedged', async () => {
-    useProbeClock()
-    mocks.mode = 'outbox'
-    mocks.submissions = []
-    mocks.call.mockRejectedValueOnce(new Error('socket closed')).mockResolvedValue({
-      ok: true,
-      value: { submission: { clientMessageId: 'client-1', dispatchState: 'accepted' } }
-    })
-
-    render(
-      <NativeChatStructuredSession
-        isVisible
-        isFocusedGroup
-        tabId="structured-tab-wedge"
-        sessionId="session-wedge"
-        target={{ kind: 'local' }}
-        agent="codex"
-      />
-    )
-
-    const send = mocks.composerProps?.structuredTransport?.send as
-      | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
-      | undefined
-    await act(async () => {
-      expect(send?.('first', [])).toBe(true)
-    })
-    expect(mocks.call).toHaveBeenCalledOnce()
-    expect(screen.getByText('Message delivery is unconfirmed.')).toBeTruthy()
-
-    await act(async () => {
-      expect(send?.('second', [])).toBe(true)
-    })
-    await advanceProbeClock(999)
-    expect(mocks.call).toHaveBeenCalledOnce()
-    await advanceProbeClock(1)
-    // The head is probed automatically, clears, and the queue drains.
-    expect(mocks.call).toHaveBeenCalledTimes(3)
-    expect(screen.queryByText('Message delivery is unconfirmed.')).toBeNull()
-  }, 20000)
-
-  it('probes the same operation without marking an explicit user retry', async () => {
-    useProbeClock()
-    mocks.mode = 'outbox'
-    mocks.submissions = []
-    mocks.call.mockRejectedValueOnce(new Error('socket closed')).mockResolvedValue({
-      ok: true,
-      value: { submission: { clientMessageId: 'client-1', dispatchState: 'accepted' } }
-    })
-
-    render(
-      <NativeChatStructuredSession
-        isVisible
-        isFocusedGroup
-        tabId="structured-tab-probe-flag"
-        sessionId="session-probe-flag"
-        target={{ kind: 'local' }}
-        agent="codex"
-      />
-    )
-
-    const send = mocks.composerProps?.structuredTransport?.send as
-      | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
-      | undefined
-    await act(async () => {
-      expect(send?.('first', [])).toBe(true)
-    })
-    await advanceProbeClock(999)
-    expect(mocks.call).toHaveBeenCalledOnce()
-    await advanceProbeClock(1)
-    expect(mocks.call).toHaveBeenCalledTimes(2)
-
-    const first = mocks.call.mock.calls[0]?.[2] as Record<string, unknown>
-    const probe = mocks.call.mock.calls[1]?.[2] as Record<string, unknown>
-    expect(probe.retryUnknown).toBeUndefined()
-    // Same operation id: both dedupe layers key off it.
-    expect((probe.envelope as { clientOperationId: string }).clientOperationId).toBe(
-      (first.envelope as { clientOperationId: string }).clientOperationId
-    )
-  }, 20000)
-
-  it('parks a host-confirmed unknown instead of probing it', async () => {
-    useProbeClock()
-    mocks.mode = 'outbox'
-    mocks.call.mockRejectedValueOnce(new Error('socket closed')).mockResolvedValue({
-      ok: true,
-      value: { submission: { clientMessageId: 'client-1', dispatchState: 'accepted' } }
-    })
-
-    render(
-      <NativeChatStructuredSession
-        isVisible
-        isFocusedGroup
-        tabId="structured-tab-parked"
-        sessionId="session-parked"
-        target={{ kind: 'local' }}
-        agent="codex"
-      />
-    )
-
-    const send = mocks.composerProps?.structuredTransport?.send as
-      | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
-      | undefined
-    await act(async () => {
-      expect(send?.('first', [])).toBe(true)
-    })
-    expect(mocks.call).toHaveBeenCalledOnce()
-
-    const sent = mocks.call.mock.calls[0]?.[2] as { envelope: { clientOperationId: string } }
-    // The host now reports an unresolved unknown: another replay is the user's call.
-    mocks.submissions = [
-      {
-        clientMessageId: sent.envelope.clientOperationId,
-        fence: 1,
-        payloadFingerprint: 'fp',
-        dispatchState: 'unknown',
-        providerItemId: null,
-        reason: null,
-        submittedAt: 1,
-        resolvedAt: null
-      }
-    ]
-    // Queue a second message purely to re-render so the effect observes the
-    // new submissions; it must stay wedged behind the parked head.
-    await act(async () => {
-      send?.('second', [])
-    })
-    await advanceProbeClock(3000)
-    expect(mocks.call).toHaveBeenCalledOnce()
-  }, 20000)
-
-  it('still probes while streaming batches rebuild the submissions array', async () => {
-    useProbeClock()
-    mocks.mode = 'outbox'
-    mocks.submissions = []
-    mocks.call.mockRejectedValueOnce(new Error('socket closed')).mockResolvedValue({
-      ok: true,
-      value: { submission: { clientMessageId: 'client-1', dispatchState: 'accepted' } }
-    })
-
-    const makeView = (): React.ReactElement => (
-      <NativeChatStructuredSession
-        isVisible
-        isFocusedGroup
-        tabId="structured-tab-churn"
-        sessionId="session-churn"
-        target={{ kind: 'local' }}
-        agent="codex"
-      />
-    )
-    const { rerender } = render(makeView())
-
-    const send = mocks.composerProps?.structuredTransport?.send as
-      | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
-      | undefined
-    await act(async () => {
-      expect(send?.('first', [])).toBe(true)
-    })
-    expect(mocks.call).toHaveBeenCalledOnce()
-
-    // Each batch mints a fresh submissions array for an unrelated message. An
-    // array-identity dependency restarts the backoff on every one of these, so a
-    // stream that outlasts the delay would never let the probe fire.
-    for (let index = 0; index < 12; index += 1) {
-      mocks.submissions = [
-        {
-          clientMessageId: `other-${index}`,
-          fence: 1,
-          payloadFingerprint: 'fp',
-          dispatchState: 'accepted',
-          providerItemId: null,
-          reason: null,
-          submittedAt: index,
-          resolvedAt: index
-        }
-      ]
-      await act(async () => {
-        rerender(makeView())
-        await vi.advanceTimersByTimeAsync(250)
-      })
-    }
-
-    // Asserted with no trailing grace period: the probe must have fired *during*
-    // the stream, not after it went quiet.
-    expect(mocks.call).toHaveBeenCalledTimes(2)
-  }, 20000)
-
-  it('restarts probe delay when the runtime target changes', async () => {
-    useProbeClock()
-    mocks.mode = 'outbox'
-    mocks.call.mockRejectedValueOnce(new Error('socket closed')).mockResolvedValue({
-      ok: true,
-      value: { submission: { clientMessageId: 'client-1', dispatchState: 'accepted' } }
-    })
-
-    const makeView = (
-      target: { kind: 'local' } | { kind: 'environment'; environmentId: string }
-    ) => (
-      <NativeChatStructuredSession
-        isVisible
-        isFocusedGroup
-        tabId="structured-tab-target-switch"
-        sessionId="session-target-switch"
-        target={target}
-        agent="codex"
-      />
-    )
-    const { rerender } = render(makeView({ kind: 'local' }))
-    const send = mocks.composerProps?.structuredTransport?.send as
-      | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
-      | undefined
-    await act(async () => {
-      expect(send?.('first', [])).toBe(true)
-    })
-    expect(mocks.call).toHaveBeenCalledOnce()
-    expect(screen.getByText('Message delivery is unconfirmed.')).toBeTruthy()
-
-    await advanceProbeClock(300)
-    rerender(makeView({ kind: 'environment', environmentId: 'env-1' }))
-    await advanceProbeClock(600)
-    expect(mocks.call).toHaveBeenCalledOnce()
-    await advanceProbeClock(399)
-    expect(mocks.call).toHaveBeenCalledOnce()
-    await advanceProbeClock(1)
-    expect(mocks.call).toHaveBeenCalledTimes(2)
-  }, 10000)
-
-  it('never auto-probes an entry the user already force-retried', async () => {
-    useProbeClock()
-    mocks.mode = 'outbox'
-    mocks.submissions = []
-    // Both the original send and the user's explicit Retry fail at the transport.
-    mocks.call.mockRejectedValue(new Error('socket closed'))
-
-    render(
-      <NativeChatStructuredSession
-        isVisible
-        isFocusedGroup
-        tabId="structured-tab-forced"
-        sessionId="session-forced"
-        target={{ kind: 'local' }}
-        agent="codex"
-      />
-    )
-
-    const send = mocks.composerProps?.structuredTransport?.send as
-      | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
-      | undefined
-    await act(async () => {
-      expect(send?.('first', [])).toBe(true)
-    })
-    expect(mocks.call).toHaveBeenCalledOnce()
-    expect(screen.getByText('Message delivery is unconfirmed.')).toBeTruthy()
-
-    // User retries with the same envelope and no legacy redelivery signal.
-    await act(async () => {
-      fireEvent.click(screen.getByRole('button', { name: /Retry/ }))
-    })
-    expect(mocks.call).toHaveBeenCalledTimes(2)
-    const forcedRequest = mocks.call.mock.calls[1]?.[2] as Record<string, unknown> | undefined
-    expect(forcedRequest?.retryUnknown).toBeUndefined()
-
-    // That retry also failed at the transport. The probe must not repeat an
-    // explicit retry automatically.
-    await advanceProbeClock(3000)
-    expect(mocks.call).toHaveBeenCalledTimes(2)
-  }, 20000)
-
-  it('does not hot-loop when the host answers pending', async () => {
-    useProbeClock()
-    mocks.mode = 'outbox'
-    mocks.call.mockResolvedValue({
-      ok: true,
-      value: { submission: { clientMessageId: 'client-1', dispatchState: 'pending' } }
-    })
-
-    render(
-      <NativeChatStructuredSession
-        isVisible
-        isFocusedGroup
-        tabId="structured-tab-pending"
-        sessionId="session-pending"
-        target={{ kind: 'local' }}
-        agent="codex"
-      />
-    )
-
-    const send = mocks.composerProps?.structuredTransport?.send as
-      | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
-      | undefined
-    await act(async () => {
-      expect(send?.('first', [])).toBe(true)
-    })
-    expect(mocks.call).toHaveBeenCalledOnce()
-
-    // A host-pending entry stays parked until the journal answers it.
-    await advanceProbeClock(999)
-    expect(mocks.call).toHaveBeenCalledOnce()
-    await advanceProbeClock(1)
-    expect(mocks.call).toHaveBeenCalledOnce()
-    await advanceProbeClock(1500)
-    expect(mocks.call).toHaveBeenCalledOnce()
-  }, 20000)
-
-  it('keeps probing past the old five-attempt budget', async () => {
-    mocks.mode = 'outbox'
-    mocks.call.mockRejectedValue(new Error('socket closed'))
-    vi.useFakeTimers({ shouldAdvanceTime: true })
-    try {
-      render(
-        <NativeChatStructuredSession
-          isVisible
-          isFocusedGroup
-          tabId="structured-tab-budget"
-          sessionId="session-budget"
-          target={{ kind: 'local' }}
-          agent="codex"
-        />
-      )
-
-      const send = mocks.composerProps?.structuredTransport?.send as
-        | ((text: string, attachments: readonly { id: string; path: string }[]) => boolean)
-        | undefined
-      expect(send?.('first', [])).toBe(true)
-
-      // Backoff is 1+2+4+8+16 = 31s for five probes, which was the old hard budget.
-      // Step past it; a seventh call proves the probe re-arms instead of giving up.
-      for (let step = 0; step < 12; step += 1) {
-        await act(async () => {
-          await vi.advanceTimersByTimeAsync(8_000)
-        })
-      }
-      expect(mocks.call.mock.calls.length).toBeGreaterThanOrEqual(7)
-    } finally {
-      vi.useRealTimers()
-    }
-  }, 30000)
-
   // A cause seen while the chat was open is worded in full; one read back after the chat is
   // reopened may have cleared, until a Retry it still stops brings it back.
   it('words a refusal seen here in full, and after a reopen only once its Retry is refused', async () => {
diff --git a/src/renderer/src/components/native-chat/structured-agent-session-delivery-notices.test.ts b/src/renderer/src/components/native-chat/structured-agent-session-delivery-notices.test.ts
index 9e3cfedbdd1..9054c35b533 100644
--- a/src/renderer/src/components/native-chat/structured-agent-session-delivery-notices.test.ts
+++ b/src/renderer/src/components/native-chat/structured-agent-session-delivery-notices.test.ts
@@ -37,6 +37,8 @@ function entry(
 }
 
 const NOT_FAILED_HERE: ReadonlySet<string> = new Set()
+// What the row shows, quietly in place of its time, while nothing has confirmed the message.
+const SENDING = 'Sending…'
 
 function texts(
   outbox: StructuredAgentSessionOutboxEntry[],
@@ -52,7 +54,9 @@ function texts(
     startFailures,
     new Set(outbox.map((candidate) => candidate.clientMessageId))
   )
-  return Object.fromEntries([...notices].map(([id, notice]) => [id, notice.text]))
+  return Object.fromEntries(
+    [...notices].map(([id, notice]) => [id, notice.sending ? SENDING : notice.text])
+  )
 }
 
 describe('the notice on each message that did not go through', () => {
@@ -173,7 +177,9 @@ describe('the notice on each message that did not go through', () => {
   })
 
   it('says a message is unconfirmed, and only that it was not sent when nothing more is known', () => {
-    expect(texts([entry('doubt', { state: 'unconfirmed' })])).toEqual({
+    expect(
+      texts([entry('doubt', { state: 'unconfirmed', retryAfterUnknownSubmittedAt: -1 })])
+    ).toEqual({
       [agentJournalSubmissionKey('doubt')]: 'Message delivery is unconfirmed.'
     })
     expect(texts([entry('bare', { state: 'rejected' })])).toEqual({
@@ -193,21 +199,24 @@ describe('the notice on each message that did not go through', () => {
   })
 
   // The drain's own rule: a message behind the one the queue stopped on is only waiting, so it says
-  // nothing. A rejected or refused message holds nothing up and keeps its words.
+  // only that it is still sending. A rejected or refused message holds nothing up and keeps its words.
   it('says why on the message the queue stopped on and on every rejected or refused one', () => {
     expect(
       texts([
         entry('sent', { state: 'dispatching' }),
         entry('rejected', { state: 'rejected' }),
         entry('failed', { lastFailure: { kind: 'failed' } }),
-        entry('stuck', { state: 'unconfirmed' }),
+        entry('stuck', { state: 'unconfirmed', retryAfterUnknownSubmittedAt: -1 }),
         entry('behind', { state: 'unconfirmed' }),
         entry('queued')
       ])
     ).toEqual({
+      [agentJournalSubmissionKey('sent')]: SENDING,
       [agentJournalSubmissionKey('rejected')]: 'Message was not sent.',
       [agentJournalSubmissionKey('failed')]: 'Your message was not sent.',
-      [agentJournalSubmissionKey('stuck')]: 'Message delivery is unconfirmed.'
+      [agentJournalSubmissionKey('stuck')]: 'Message delivery is unconfirmed.',
+      [agentJournalSubmissionKey('behind')]: SENDING,
+      [agentJournalSubmissionKey('queued')]: SENDING
     })
   })
 
@@ -215,7 +224,10 @@ describe('the notice on each message that did not go through', () => {
   it('keeps a rejected message behind the stopped one its words but not its Retry', () => {
     const retry = vi.fn()
     for (const outbox of [
-      [entry('stuck', { state: 'unconfirmed' }), entry('rejected', { state: 'rejected' })],
+      [
+        entry('stuck', { state: 'unconfirmed', retryAfterUnknownSubmittedAt: -1 }),
+        entry('rejected', { state: 'rejected' })
+      ],
       [entry('held', { outlivedStop: true }), entry('rejected', { state: 'rejected' })]
     ]) {
       const notices = structuredAgentSessionDeliveryNotices(
@@ -234,7 +246,7 @@ describe('the notice on each message that did not go through', () => {
 
   // Ahead of the stopped message, its Retry sends it at once, so the row offers it.
   it.each([
-    ['in doubt', { state: 'unconfirmed' as const }],
+    ['in doubt', { state: 'unconfirmed' as const, retryAfterUnknownSubmittedAt: -1 }],
     ['outlived by a Stop', { outlivedStop: true as const }]
   ])('gives a failed message ahead of one %s its Retry', (_label, patch) => {
     const retry = vi.fn()
@@ -473,8 +485,231 @@ describe('the notice on each message that did not go through', () => {
     )
   })
 
-  it('says nothing on a message that is only waiting its turn or on its way', () => {
-    expect(texts([entry('queued'), entry('sending', { state: 'dispatching' })])).toEqual({})
+  it('says only that a message waiting its turn or on its way is still sending', () => {
+    const notices = structuredAgentSessionDeliveryNotices(
+      [entry('queued'), entry('sending', { state: 'dispatching' })],
+      'Claude',
+      vi.fn(),
+      [],
+      [],
+      NOT_FAILED_HERE
+    )
+    expect([...notices.values()]).toEqual([{ sending: true }, { sending: true }])
+  })
+
+  // Any row the host holds for it is the answer, whatever its state; the row itself then shows it.
+  it.each(['pending', 'accepted'] as const)(
+    'stops saying a message is sending once the journal holds a %s row for it',
+    (dispatchState) => {
+      const answer = (clientMessageId: string): AgentJournalSubmission => ({
+        clientMessageId,
+        fence: 1,
+        payloadFingerprint: 'fp',
+        dispatchState,
+        providerItemId: null,
+        reason: null,
+        submittedAt: 1,
+        resolvedAt: null
+      })
+      const resent = entry('resent', { state: 'unconfirmed', lastAttemptAt: 1 })
+      const outbox = [entry('queued'), entry('sending', { state: 'dispatching' }), resent]
+      expect(texts(outbox)).toEqual({
+        [agentJournalSubmissionKey('queued')]: SENDING,
+        [agentJournalSubmissionKey('sending')]: SENDING,
+        [agentJournalSubmissionKey('resent')]: SENDING
+      })
+      expect(texts(outbox, [answer('queued'), answer('sending'), answer('resent')])).toEqual({})
+      // Read as the outbox will commit it, so the resent one never says it failed on the way.
+      expect(texts([resent], [answer('resent')])).toEqual({})
+    }
+  )
+
+  // Only a row that has the message ends it; one in doubt leaves it looking sent.
+  describe('a message whose journal row does not have it yet', () => {
+    const row = (
+      clientMessageId: string,
+      dispatchState: AgentJournalSubmission['dispatchState'],
+      patch: Partial<AgentJournalSubmission> = {}
+    ): AgentJournalSubmission => ({
+      clientMessageId,
+      fence: 1,
+      payloadFingerprint: 'fp',
+      dispatchState,
+      providerItemId: null,
+      reason: null,
+      submittedAt: 7,
+      resolvedAt: null,
+      ...patch
+    })
+    const stuck = entry('stuck', { state: 'unconfirmed', retryAfterUnknownSubmittedAt: -1 })
+
+    it.each([
+      ['queued', { state: 'queued' as const }, {}],
+      ['in flight', { state: 'dispatching' as const, lastAttemptAt: 2 }, {}],
+      [
+        'in flight, after a host restart',
+        { state: 'dispatching' as const, lastAttemptAt: 2 },
+        { recovered: true as const }
+      ]
+    ])('says it is sending while your Retry is %s', (_label, patch, rowPatch) => {
+      const doubt = row('m', 'unknown', rowPatch)
+      expect(texts([entry('m', { state: 'unconfirmed', lastAttemptAt: 1 })], [doubt])).toEqual({
+        [agentJournalSubmissionKey('m')]: 'Message delivery is unconfirmed.'
+      })
+      const retried = entry('m', { lastAttemptAt: 1, retryAfterUnknownSubmittedAt: 7, ...patch })
+      expect(texts([retried], [doubt])).toEqual({ [agentJournalSubmissionKey('m')]: SENDING })
+    })
+
+    it.each([
+      ['a live unknown', {}],
+      ['a recovered unknown', { recovered: true as const }]
+    ])('says the second of two in doubt is sending when each row holds %s', (_label, patch) => {
+      const a = entry('a', { state: 'unconfirmed' })
+      const b = entry('b', { state: 'unconfirmed' })
+      expect(texts([a, b], [row('a', 'unknown', patch), row('b', 'unknown', patch)])).toEqual({
+        [agentJournalSubmissionKey('a')]: 'Message delivery is unconfirmed.',
+        [agentJournalSubmissionKey('b')]: SENDING
+      })
+    })
+
+    // The rejection makes it the host's: not sent, in the host's words, whether its outbox copy or
+    // its loaded row draws it.
+    it('says a requeued message whose row was rejected was not sent, never sending', () => {
+      const requeued = entry('q', { state: 'queued', lastAttemptAt: 1 })
+      const rejected = row('q', 'rejected', { reason: 'provider said no', resolvedAt: 8 })
+      const notSent = { [agentJournalSubmissionKey('q')]: 'provider said no' }
+      expect(texts([requeued], [rejected])).toEqual(notSent)
+      expect(texts([stuck, requeued], [rejected])).toEqual({
+        [agentJournalSubmissionKey('stuck')]: 'Message delivery is unconfirmed.',
+        ...notSent
+      })
+      const loadedRow: AgentJournalRenderItem = {
+        itemId: agentJournalSubmissionKey('q'),
+        revision: 1,
+        sequence: 1,
+        observedAt: 8,
+        body: { kind: 'message', role: 'user', blocks: [{ type: 'text', text: 'q' }] }
+      }
+      const loaded = structuredAgentSessionDeliveryNotices(
+        [requeued],
+        'Claude',
+        vi.fn(),
+        [rejected],
+        [],
+        NOT_FAILED_HERE,
+        [],
+        new Set(),
+        [loadedRow]
+      )
+      expect([...loaded]).toEqual([[agentJournalSubmissionKey('q'), { text: 'provider said no' }]])
+    })
+  })
+
+  // One state, one surface: a row that says it did not go through never also says it is sending.
+  it.each([
+    ['rejected', entry('m', { state: 'rejected' }), []],
+    ['held for its Retry', entry('m', { lastFailure: { kind: 'failed' } }), []],
+    [
+      'in doubt with a row the host holds',
+      entry('m', { state: 'unconfirmed', lastAttemptAt: 1 }),
+      [
+        {
+          clientMessageId: 'm',
+          fence: 1,
+          payloadFingerprint: 'fp',
+          dispatchState: 'unknown',
+          providerItemId: null,
+          reason: null,
+          submittedAt: 1,
+          resolvedAt: null
+        } satisfies AgentJournalSubmission
+      ]
+    ],
+    [
+      'retried by the user',
+      entry('m', { state: 'unconfirmed', retryAfterUnknownSubmittedAt: 1 }),
+      []
+    ],
+    ['outlived by a Stop', entry('m', { state: 'unconfirmed', outlivedStop: true }), []]
+  ])('says only why on a message %s, never that it is sending', (_label, failed, rows) => {
+    const notice = structuredAgentSessionDeliveryNotices(
+      [failed],
+      'Claude',
+      vi.fn(),
+      rows,
+      [],
+      NOT_FAILED_HERE
+    ).get(agentJournalSubmissionKey('m'))
+    expect(notice?.sending).toBeUndefined()
+    expect(notice?.text).toMatch(/not sent|unconfirmed/)
+    expect(notice?.onRetry).toBeDefined()
+  })
+
+  // The unconfirmed probe resends it under its own id until the journal answers, so the row says
+  // it is still sending, with no Retry, until a row lands.
+  describe('a message in doubt that Orca resends on its own', () => {
+    const doubt = (patch: Partial<StructuredAgentSessionOutboxEntry> = {}) =>
+      entry('doubt', { state: 'unconfirmed', lastAttemptAt: 1, ...patch })
+    const row = (patch: Partial<AgentJournalSubmission>): AgentJournalSubmission => ({
+      clientMessageId: 'doubt',
+      fence: 1,
+      payloadFingerprint: 'fp',
+      dispatchState: 'unknown',
+      providerItemId: null,
+      reason: null,
+      submittedAt: 1,
+      resolvedAt: null,
+      ...patch
+    })
+    const UNCONFIRMED = { [agentJournalSubmissionKey('doubt')]: 'Message delivery is unconfirmed.' }
+
+    it('says only that it is still sending while the journal holds no row for it', () => {
+      const notices = structuredAgentSessionDeliveryNotices(
+        [doubt(), entry('behind')],
+        'Claude',
+        vi.fn(),
+        [],
+        [],
+        NOT_FAILED_HERE
+      )
+      expect(notices.get(agentJournalSubmissionKey('doubt'))).toEqual({ sending: true })
+      expect(notices.get(agentJournalSubmissionKey('behind'))).toEqual({ sending: true })
+      // Another message's row is not its answer.
+      expect(
+        texts([doubt()], [row({ clientMessageId: 'other', dispatchState: 'accepted' })])
+      ).toEqual({ [agentJournalSubmissionKey('doubt')]: SENDING })
+    })
+
+    it.each([
+      ['a live unknown', row({})],
+      ['a recovered unknown', row({ recovered: true })],
+      [
+        "an older host's recovered unknown",
+        row({ reason: 'host_restarted_before_acknowledgement' })
+      ]
+    ])('says it is unconfirmed, with its Retry, once the journal holds %s', (_label, answer) => {
+      const retry = vi.fn()
+      const notices = structuredAgentSessionDeliveryNotices(
+        [doubt()],
+        'Claude',
+        retry,
+        [answer],
+        [],
+        NOT_FAILED_HERE
+      )
+      expect(Object.fromEntries([...notices].map(([id, notice]) => [id, notice.text]))).toEqual(
+        UNCONFIRMED
+      )
+      notices.get(agentJournalSubmissionKey('doubt'))?.onRetry?.()
+      expect(retry).toHaveBeenCalledExactlyOnceWith('doubt')
+    })
+
+    it.each([
+      ['the user already retried', { retryAfterUnknownSubmittedAt: 1 }],
+      ['a Stop outlived', { outlivedStop: true as const }]
+    ])('says it is unconfirmed when %s it, as nothing resends it', (_label, patch) => {
+      expect(texts([doubt(patch)])).toEqual(UNCONFIRMED)
+    })
   })
 
   // Matched on the typed fact of a row found by its identity, never on either sentence.
diff --git a/src/renderer/src/components/native-chat/structured-agent-session-delivery-notices.ts b/src/renderer/src/components/native-chat/structured-agent-session-delivery-notices.ts
index 1ef4067357d..52f3832dffa 100644
--- a/src/renderer/src/components/native-chat/structured-agent-session-delivery-notices.ts
+++ b/src/renderer/src/components/native-chat/structured-agent-session-delivery-notices.ts
@@ -1,11 +1,14 @@
-// Which of the structured chat's own messages say, on their row, that they did not go through.
+// Which of the structured chat's own messages say, on their row, that they did not go through, and
+// which say quietly that they are still sending: every other one, until the host holds a row that
+// has it (pending or accepted). A row in doubt does not, so a message resent over one still reads
+// as sending; a rejected row makes it the host's, shown as not sent.
 //
 // Derived from the outbox on every render and never stored: each failed or held message carries
 // its own typed failure, so each row words its own reason. Read through the drain's own rule: while
 // the queue is stopped, the message it stopped on and any failed one ahead of it have a Retry, as
-// each would go out at once; one behind it would wait unseen. One waiting behind says nothing; a
-// rejected or refused message holds nothing up, so it keeps its words and gets its Retry once the
-// queue moves.
+// each would go out at once; one behind it would wait unseen. One waiting behind has no failure of
+// its own, so it reads as sending; a rejected or refused message holds nothing up, so it keeps its
+// words and gets its Retry once the queue moves.
 //
 // A message the host recorded and then rejected is drawn from the host's history, worded from the
 // journal's own fact, with no Retry: sending it again is a new message. A rejection that is a
@@ -34,6 +37,8 @@ import {
   admitStructuredAgentSessionOutboxEntry,
   structuredAgentSessionEntryHeldForRetry
 } from '../../../../shared/structured-agent-session-outbox-admission'
+import { reconcileStructuredAgentSessionOutboxWithQueue } from '../../../../shared/structured-agent-session-draft-hand-off'
+import { structuredAgentSessionEntryResendsUnconfirmed } from '../../../../shared/structured-agent-session-outbox-unconfirmed-resend'
 import type { AgentSessionFailureWordsContext } from '../../../../shared/agent-session-failure-words'
 import {
   structuredAgentSessionAttemptFailureParts,
@@ -44,7 +49,10 @@ import { translate } from '@/i18n/i18n'
 import { agentSessionWriteNoticeText } from './agent-session-write-notice-text'
 import type { NativeChatDeliveryNotice } from './NativeChatMessageRow'
 
+/** One shared value, so a rebuilt map re-renders no row still sending. */
+const STRUCTURED_AGENT_SESSION_DELIVERY_SENDING: NativeChatDeliveryNotice = { sending: true }
 const NO_COMMANDS: ReadonlySet<string> = new Set()
+const NO_ITEMS: readonly AgentJournalRenderItem[] = []
 
 /** The facts the chat's loaded start-failure rows state. */
 export function structuredAgentSessionStartFailureFacts(
@@ -149,7 +157,8 @@ export function structuredAgentSessionDeliveryNotices(
   outbox: readonly StructuredAgentSessionOutboxEntry[],
   agentName: string,
   retry: (clientMessageId: string) => void,
-  /** The journal's rows, whose rejected ones carry more of a rejection than the message keeps. */
+  /** The journal's rows: rejected ones carry more of a rejection than the message keeps, and a
+   *  message with no pending or accepted one is still sending. */
   submissions: readonly AgentJournalSubmission[],
   /** What the loaded start-failure rows state, from `structuredAgentSessionStartFailureFacts`. */
   startFailures: readonly AgentSessionFailureFact[],
@@ -158,22 +167,28 @@ export function structuredAgentSessionDeliveryNotices(
   /** The queue's live cards, which the transcript leaves a rejected message to. */
   queuedMessageIds: readonly string[] = [],
   /** The loaded commands, from `structuredAgentSessionCommandItemIds`: they report their own. */
-  commandItemIds: ReadonlySet<string> = NO_COMMANDS
+  commandItemIds: ReadonlySet<string> = NO_COMMANDS,
+  /** The loaded rows: a rejected message's outbox copy leaves once its row is here. */
+  journalItems: readonly AgentJournalRenderItem[] = NO_ITEMS
 ): ReadonlyMap<string, NativeChatDeliveryNotice> {
-  const admission = admitStructuredAgentSessionOutboxEntry(outbox)
+  // As the transcript reads it, so a row that lands is answered here before the outbox commits it.
+  const entries = reconcileStructuredAgentSessionOutboxWithQueue(outbox, submissions, journalItems)
+  const admission = admitStructuredAgentSessionOutboxEntry(entries)
   const held = admission.state === 'blocked' ? admission.entry.clientMessageId : null
-  const stalledFrom = admission.state === 'blocked' ? outbox.indexOf(admission.entry) : -1
+  const stalledFrom = admission.state === 'blocked' ? entries.indexOf(admission.entry) : -1
   const rejected = new Map(
     submissions
       .filter((submission) => submission.dispatchState === 'rejected')
       .map((submission) => [submission.clientMessageId, submission])
   )
   const notices = new Map<string, NativeChatDeliveryNotice>()
-  for (const [index, entry] of outbox.entries()) {
+  for (const [index, entry] of entries.entries()) {
+    // Resent under its own id until the journal answers, so still sending, not failed.
     if (
-      entry.state === 'rejected' ||
-      structuredAgentSessionEntryHeldForRetry(entry) ||
-      entry.clientMessageId === held
+      !structuredAgentSessionEntryResendsUnconfirmed(entry, submissions) &&
+      (entry.state === 'rejected' ||
+        structuredAgentSessionEntryHeldForRetry(entry) ||
+        entry.clientMessageId === held)
     ) {
       // Its own Retry is the step, so the words leave out sending again. One the host recorded is
       // the host's: sending it again is a new message, so it has no Retry.
@@ -185,6 +200,17 @@ export function structuredAgentSessionDeliveryNotices(
         agentJournalSubmissionKey(entry.clientMessageId),
         retryControl ? { text, onRetry: () => retry(entry.clientMessageId) } : { text }
       )
+    } else if (
+      !submissions.some(
+        (submission) =>
+          submission.clientMessageId === entry.clientMessageId &&
+          (submission.dispatchState === 'pending' || submission.dispatchState === 'accepted')
+      )
+    ) {
+      notices.set(
+        agentJournalSubmissionKey(entry.clientMessageId),
+        STRUCTURED_AGENT_SESSION_DELIVERY_SENDING
+      )
     }
   }
   // After the outbox's: in the host's words, whether its row or the outbox's copy draws it.
diff --git a/src/renderer/src/components/native-chat/use-structured-agent-session-delivery-notices.ts b/src/renderer/src/components/native-chat/use-structured-agent-session-delivery-notices.ts
index 26cdd00fb81..2c39d306e82 100644
--- a/src/renderer/src/components/native-chat/use-structured-agent-session-delivery-notices.ts
+++ b/src/renderer/src/components/native-chat/use-structured-agent-session-delivery-notices.ts
@@ -11,6 +11,7 @@ import { useStructuredAgentSessionStartFailureFacts } from './use-structured-age
 import type { NativeChatDeliveryNotice } from './NativeChatMessageRow'
 
 const NO_SUBMISSIONS: readonly AgentJournalSubmission[] = []
+const NO_ITEMS: readonly AgentJournalRenderItem[] = []
 
 /** The structured chat's delivery notices, by the message id each row renders under. */
 export function useStructuredAgentSessionDeliveryNotices(args: {
@@ -31,14 +32,17 @@ export function useStructuredAgentSessionDeliveryNotices(args: {
   const retry = useCallback((clientMessageId: string) => {
     retryRef.current(clientMessageId)
   }, [])
-  // Only a message shown as not sent reads the journal's rows (a withdrawn one draws nothing), so
-  // in a chat without one a new batch of them re-renders no row.
+  // Only a message shown as not sent (a withdrawn one draws nothing) or still in the outbox reads
+  // the journal's rows, so in a chat with neither a new batch of them re-renders no row.
   const hasRejected =
     outbox.some((entry) => entry.state === 'rejected') ||
     submissions.some(
       (submission) => submission.dispatchState === 'rejected' && !dispatchWasWithdrawn(submission)
     )
-  const rejectionRows = hasRejected ? submissions : NO_SUBMISSIONS
+  const journalRows = hasRejected || outbox.length > 0 ? submissions : NO_SUBMISSIONS
+  // Only an outbox copy of a rejected message reads the loaded rows, so a streaming turn rebuilds
+  // no notice otherwise.
+  const loadedItems = hasRejected && outbox.length > 0 ? args.journalItems : NO_ITEMS
   const startFailures = useStructuredAgentSessionStartFailureFacts(args.journalItems, hasRejected)
   const commandItemIds = useCommandItemIds(args.journalItems, hasRejected)
   const notices = useMemo(
@@ -47,21 +51,23 @@ export function useStructuredAgentSessionDeliveryNotices(args: {
         outbox,
         agentName,
         retry,
-        rejectionRows,
+        journalRows,
         startFailures,
         failedHere,
         queuedMessageIds,
-        commandItemIds
+        commandItemIds,
+        loadedItems
       ),
     [
       outbox,
       agentName,
       retry,
-      rejectionRows,
+      journalRows,
       startFailures,
       failedHere,
       queuedMessageIds,
-      commandItemIds
+      commandItemIds,
+      loadedItems
     ]
   )
   // A submission batch rebuilds the map; one that says the same keeps the old, so no row re-renders.
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 1d70ad86b88..819995bee0f 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 { structuredAgentSessionEntryResendsUnconfirmed } from '../../../../shared/structured-agent-session-outbox-unconfirmed-resend'
 import {
   commitStructuredAgentSessionOutbox,
   getStructuredAgentSessionOutbox
@@ -40,17 +41,15 @@ export function useStructuredAgentSessionOutboxUnconfirmedProbe(args: {
   // A non-null `retryAfterUnknownSubmittedAt` means the user already retried, so
   // another request would repeat that explicit action. Only entries that have
   // never been retried, and that no Stop outlived, are safe to probe automatically.
+  // The delivery notices read the same rule: while it is resent here, its row says it is sending.
   const probeId =
     blocker &&
     blocker.sessionId === sessionId &&
-    blocker.retryAfterUnknownSubmittedAt === null &&
-    blocker.outlivedStop !== true
+    structuredAgentSessionEntryResendsUnconfirmed(blocker, submissions)
       ? blocker.clientMessageId
       : null
-  const probeSettled =
-    probeId !== null && submissions.some((submission) => submission.clientMessageId === probeId)
   useEffect(() => {
-    if (probeId === null || probeSettled || !owner.attached) {
+    if (probeId === null || !owner.attached) {
       return
     }
     const attempts = probeAttemptsRef.current.id === probeId ? probeAttemptsRef.current.attempts : 0
@@ -70,5 +69,5 @@ export function useStructuredAgentSessionOutboxUnconfirmedProbe(args: {
       Math.min(UNCONFIRMED_PROBE_BASE_DELAY_MS * 2 ** attempts, UNCONFIRMED_PROBE_MAX_DELAY_MS)
     )
     return () => clearTimeout(timer)
-  }, [owner.attached, owner.ownerChange, owner.targetKey, probeId, probeSettled, sessionId])
+  }, [owner.attached, owner.ownerChange, owner.targetKey, probeId, sessionId])
 }
diff --git a/src/renderer/src/i18n/locales/en.json b/src/renderer/src/i18n/locales/en.json
index d0c8356d42a..0004adf383b 100644
--- a/src/renderer/src/i18n/locales/en.json
+++ b/src/renderer/src/i18n/locales/en.json
@@ -18067,6 +18067,7 @@
       "dismissDeliveryNotice": "Dismiss",
       "messageNotSent": "Message not sent",
       "deliveryUnconfirmed": "Delivery unconfirmed — check chat before retrying",
+      "messageSending": "Sending…",
       "queuedMessages": {
         "behindReturnedHold": "Waiting — a message ahead needs attention",
         "awaitingAnswerHold": "Waiting for your answer",
diff --git a/src/renderer/src/i18n/locales/es.json b/src/renderer/src/i18n/locales/es.json
index 1367930a63f..8b224926b3e 100644
--- a/src/renderer/src/i18n/locales/es.json
+++ b/src/renderer/src/i18n/locales/es.json
@@ -15192,6 +15192,7 @@
       "dismissDeliveryNotice": "Descartar",
       "messageNotSent": "Mensaje no enviado",
       "deliveryUnconfirmed": "Entrega sin confirmar — revisa el chat antes de reintentar",
+      "messageSending": "Enviando…",
       "subagents": {
         "unnamed": "Subagente"
       },
diff --git a/src/renderer/src/i18n/locales/fr.json b/src/renderer/src/i18n/locales/fr.json
index f234d603be9..beb91b07eca 100644
--- a/src/renderer/src/i18n/locales/fr.json
+++ b/src/renderer/src/i18n/locales/fr.json
@@ -17880,6 +17880,7 @@
       "dismissDeliveryNotice": "Ignorer",
       "messageNotSent": "Message non envoyé",
       "deliveryUnconfirmed": "Livraison non confirmée — vérifiez le chat avant de réessayer",
+      "messageSending": "Envoi…",
       "queuedMessages": {
         "alreadySent": "Ce message a déjà été envoyé.",
         "editAlreadySent": "Déjà envoyé — votre texte reste dans la zone de saisie.",
diff --git a/src/renderer/src/i18n/locales/ja.json b/src/renderer/src/i18n/locales/ja.json
index 45fd93595fa..30cfa9d7051 100644
--- a/src/renderer/src/i18n/locales/ja.json
+++ b/src/renderer/src/i18n/locales/ja.json
@@ -17817,6 +17817,7 @@
       "dismissDeliveryNotice": "閉じる",
       "messageNotSent": "メッセージは送信されませんでした",
       "deliveryUnconfirmed": "配信を確認できません — 再試行する前にチャットを確認してください",
+      "messageSending": "送信中…",
       "queuedMessages": {
         "alreadySent": "このメッセージはすでに送信されています。",
         "editAlreadySent": "すでに送信されています — テキストは入力欄に残っています。",
diff --git a/src/renderer/src/i18n/locales/ko.json b/src/renderer/src/i18n/locales/ko.json
index 8f3554f0523..522a0a6de00 100644
--- a/src/renderer/src/i18n/locales/ko.json
+++ b/src/renderer/src/i18n/locales/ko.json
@@ -17817,6 +17817,7 @@
       "dismissDeliveryNotice": "닫기",
       "messageNotSent": "메시지가 전송되지 않음",
       "deliveryUnconfirmed": "전달 확인 안 됨 — 다시 시도하기 전에 채팅을 확인하세요",
+      "messageSending": "전송 중…",
       "queuedMessages": {
         "alreadySent": "이 메시지는 이미 전송되었습니다.",
         "editAlreadySent": "이미 전송되었습니다 — 텍스트는 입력창에 남아 있습니다.",
diff --git a/src/renderer/src/i18n/locales/zh.json b/src/renderer/src/i18n/locales/zh.json
index f1d77c3ee26..473fc6de55c 100644
--- a/src/renderer/src/i18n/locales/zh.json
+++ b/src/renderer/src/i18n/locales/zh.json
@@ -17834,6 +17834,7 @@
       "dismissDeliveryNotice": "关闭",
       "messageNotSent": "消息未发送",
       "deliveryUnconfirmed": "无法确认送达 — 重试前请检查聊天",
+      "messageSending": "正在发送…",
       "queuedMessages": {
         "alreadySent": "此消息已发送。",
         "editAlreadySent": "已发送 — 你的文本仍在输入框中。",
diff --git a/src/shared/structured-agent-session-outbox-unconfirmed-resend.ts b/src/shared/structured-agent-session-outbox-unconfirmed-resend.ts
new file mode 100644
index 00000000000..ee65fed7287
--- /dev/null
+++ b/src/shared/structured-agent-session-outbox-unconfirmed-resend.ts
@@ -0,0 +1,18 @@
+// Which send in doubt Orca resends on its own under the same id, without the user's Retry.
+
+import type { AgentJournalSubmission } from './agent-session-journal-types'
+import type { StructuredAgentSessionOutboxEntry } from './structured-agent-session-outbox'
+
+/** Whether the unconfirmed probe resends this entry: in doubt, never retried by the user, not
+ *  outlived by a Stop, and with no journal row yet. Any row ends it: the journal answers from there. */
+export function structuredAgentSessionEntryResendsUnconfirmed(
+  entry: StructuredAgentSessionOutboxEntry,
+  submissions: readonly AgentJournalSubmission[]
+): boolean {
+  return (
+    entry.state === 'unconfirmed' &&
+    entry.retryAfterUnknownSubmittedAt === null &&
+    entry.outlivedStop !== true &&
+    !submissions.some((submission) => submission.clientMessageId === entry.clientMessageId)
+  )
+}