fix(native-chat): show "Sending…" on a message until the host confirms it

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",

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')
+  })
 })

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 ? (

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