diff --git a/mobile/src/session/use-mobile-native-chat-controller.ts b/mobile/src/session/use-mobile-native-chat-controller.ts
index 5ed98925e..eaa36fc50 100644
--- a/mobile/src/session/use-mobile-native-chat-controller.ts
+++ b/mobile/src/session/use-mobile-native-chat-controller.ts
@@ -6,6 +6,7 @@ import {
   type MutableRefObject,
   type SetStateAction
 } from 'react'
+import { encodeNativeChatTranscriptIdentity } from '../../../src/shared/native-chat-transcript-retention'
 import { useMobileSessionViewMode } from './use-mobile-session-view-mode'
 import type { RpcClient } from '../transport/rpc-client'
 import type { ConnectionState } from '../transport/types'
@@ -153,6 +154,7 @@ export function useMobileNativeChatController(args: {
 
   const nativeChatSession = useMobileNativeChatSession({
     client,
+    sourceIdentity: encodeNativeChatTranscriptIdentity([hostId, worktreeId]),
     agent: activeChatResolution?.agent ?? null,
     sessionId: activeChatSessionId,
     transcriptPath: activeChatResolution?.transcriptPath ?? null
@@ -203,7 +205,8 @@ export function useMobileNativeChatController(args: {
   } = useMobileNativeChatPrompts({
     enabled: activeChatResolution != null,
     status: nativeChatStatus,
-    messages: nativeChatSession.messages
+    messages: nativeChatSession.messages,
+    transcriptLoading: nativeChatSession.transcriptLoading
   })
   // A never-read transcript cannot prove that a dismissed prompt cleared.
   const nativeChatTranscriptSettled =
diff --git a/mobile/src/session/use-mobile-native-chat-prompts.test.ts b/mobile/src/session/use-mobile-native-chat-prompts.test.ts
index f8a1d2a61..905b92155 100644
--- a/mobile/src/session/use-mobile-native-chat-prompts.test.ts
+++ b/mobile/src/session/use-mobile-native-chat-prompts.test.ts
@@ -15,14 +15,16 @@ const ASK = JSON.stringify({
 
 function promptsFor(
   status: Partial<AgentStatusEntry> | null,
-  messages: NativeChatMessage[] = []
+  messages: NativeChatMessage[] = [],
+  transcriptLoading = false
 ): ReturnType<typeof useMobileNativeChatPrompts> {
   let captured: ReturnType<typeof useMobileNativeChatPrompts> | undefined
   function Probe(): null {
     captured = useMobileNativeChatPrompts({
       enabled: true,
       status: status as AgentStatusEntry | null,
-      messages
+      messages,
+      transcriptLoading
     })
     return null
   }
@@ -118,6 +120,18 @@ describe('useMobileNativeChatPrompts ask state gate', () => {
     expect(promptsFor(null, askMessages).ask).not.toBeNull()
   })
 
+  it('withholds retained transcript asks while the replacement read is unsettled', () => {
+    const prompts = promptsFor({ state: 'done' }, askMessages, true)
+    expect(prompts.ask).toBeNull()
+    expect(prompts.detectedAsk).toBeNull()
+  })
+
+  it('keeps a paused live status ask authoritative while the read is unsettled', () => {
+    const prompts = promptsFor({ state: 'waiting', interactivePrompt: ASK }, askMessages, true)
+    expect(prompts.ask).toMatchObject({ questions: [{ question: 'Which path?' }] })
+    expect(prompts.detectedAsk).not.toBeNull()
+  })
+
   it('does not leak a paused-out sticky status prompt through the transcript fallback', () => {
     // The post-answer window: the status still carries the prompt while flipping
     // to `working`, and the transcript's tool-result row has not landed yet, so
diff --git a/mobile/src/session/use-mobile-native-chat-prompts.ts b/mobile/src/session/use-mobile-native-chat-prompts.ts
index 717bd505a..61b831daf 100644
--- a/mobile/src/session/use-mobile-native-chat-prompts.ts
+++ b/mobile/src/session/use-mobile-native-chat-prompts.ts
@@ -1,7 +1,7 @@
 import { useMemo } from 'react'
 import type { AgentStatusEntry } from '../../../src/shared/agent-status-types'
 import type { NativeChatMessage } from '../../../src/shared/native-chat-types'
-import { extractPendingAsk, parseAskFromStatus } from './mobile-native-chat-ask'
+import { parseAskFromStatus, resolveNativeChatAsk } from './mobile-native-chat-ask'
 import { detectAgentPermission, parseApprovalFromStatus } from './mobile-native-chat-permission'
 import { parseAgentQuestion } from './mobile-native-chat-question'
 
@@ -17,8 +17,11 @@ export function useMobileNativeChatPrompts(args: {
   enabled: boolean
   status: AgentStatusEntry | null | undefined
   messages: readonly NativeChatMessage[]
+  /** True while `messages` is an unsettled read (including the cached list held
+   *  across a reconnect). Required: an ask derived from it may already be answered. */
+  transcriptLoading: boolean
 }): MobileNativeChatPrompts {
-  const { enabled, status, messages } = args
+  const { enabled, status, messages, transcriptLoading } = args
   const blocked = status?.state === 'waiting' || status?.state === 'blocked'
   // Both permission paths sit inside the paused gate: an approval envelope can
   // outlive its answer (the host keeps it sticky), so only a waiting/blocked
@@ -38,11 +41,16 @@ export function useMobileNativeChatPrompts(args: {
     () => parseAskFromStatus(status?.interactivePrompt, status?.toolName),
     [status?.interactivePrompt, status?.toolName]
   )
-  const askFromMessages = useMemo(
-    () => (askFromStatus ? null : extractPendingAsk(messages)),
-    [askFromStatus, messages]
+  const resolvedAsk = useMemo(
+    () =>
+      resolveNativeChatAsk({
+        liveAsk: askFromStatus,
+        messages,
+        transcriptSettled: !transcriptLoading
+      }),
+    [askFromStatus, transcriptLoading, messages]
   )
-
+  const askFromMessages = askFromStatus ? null : resolvedAsk
   const detectedAsk = askFromStatus ?? askFromMessages
 
   return {
diff --git a/mobile/src/session/use-mobile-native-chat-session.test.ts b/mobile/src/session/use-mobile-native-chat-session.test.ts
index 844c311b8..8c685d002 100644
--- a/mobile/src/session/use-mobile-native-chat-session.test.ts
+++ b/mobile/src/session/use-mobile-native-chat-session.test.ts
@@ -36,6 +36,7 @@ describe('useMobileNativeChatSession', () => {
   function Harness({ client }: { client: RpcClient | null }): null {
     state = useMobileNativeChatSession({
       client,
+      sourceIdentity: 'host-a\0workspace-a',
       agent: 'claude',
       sessionId: 'session',
       transcriptPath: null
@@ -456,14 +457,17 @@ describe('useMobileNativeChatSession transcriptLoading', () => {
   function Harness({
     client,
     sessionId,
-    agent = 'claude'
+    agent = 'claude',
+    sourceIdentity = 'host-a\0workspace-a'
   }: {
     client: RpcClient | null
     sessionId: string | null
     agent?: string | null
+    sourceIdentity?: string
   }): null {
     const session = useMobileNativeChatSession({
       client,
+      sourceIdentity,
       agent,
       sessionId,
       transcriptPath: null
@@ -506,7 +510,8 @@ describe('useMobileNativeChatSession transcriptLoading', () => {
   it('re-reads instead of resurfacing a settled read when the same identity returns', async () => {
     // Leaving chat view nulls the agent, then returning restores the identity a
     // settled read already matched — but its list was cleared, so trusting it
-    // would report 'ready' over an empty transcript.
+    // would report 'ready' over an empty transcript. The last settled list for
+    // this identity keeps rendering while the re-read is in flight.
     const subscribe: RpcClient['subscribe'] = vi.fn((_method, _params, onData) => {
       onData({ type: 'snapshot', messages: [message('a-1')], hasMore: false })
       return () => {}
@@ -524,12 +529,17 @@ describe('useMobileNativeChatSession transcriptLoading', () => {
       renderer?.update(createElement(Harness, { client, sessionId: 'session-a', agent: 'claude' }))
     )
 
-    expect(renders[0]).toMatchObject({ status: 'loading', transcriptLoading: true, ids: [] })
+    expect(renders[0]).toMatchObject({
+      status: 'loading',
+      transcriptLoading: true,
+      ids: ['a-1']
+    })
   })
 
-  it('re-reads instead of resurfacing a settled read after a reconnect', async () => {
-    // A reconnect swaps the client without moving the identity; the effect
-    // re-subscribes and clears the list, so the old outcome must not stand.
+  it('keeps the last settled list rendered while a swapped client re-reads', async () => {
+    // A manual-retry reconnect swaps the client without moving the identity; the
+    // old outcome must not stand ('loading', not 'ready'), but the cached
+    // transcript keeps rendering instead of collapsing to a full-screen spinner.
     const subscribe: RpcClient['subscribe'] = vi.fn((_method, _params, onData) => {
       onData({ type: 'snapshot', messages: [message('a-1')], hasMore: false })
       return () => {}
@@ -538,13 +548,61 @@ describe('useMobileNativeChatSession transcriptLoading', () => {
     await mountAt(client, 'session-a')
     expect(renders.at(-1)).toMatchObject({ status: 'ready' })
 
-    const reconnected = { subscribe: vi.fn(() => () => {}) } as unknown as RpcClient
+    let emitFresh: (frame: unknown) => void = () => {}
+    const reconnected = {
+      subscribe: vi.fn((_method: string, _params: unknown, onData: (frame: unknown) => void) => {
+        emitFresh = onData
+        return () => {}
+      })
+    } as unknown as RpcClient
     renders.length = 0
     await act(async () =>
       renderer?.update(createElement(Harness, { client: reconnected, sessionId: 'session-a' }))
     )
 
-    expect(renders[0]).toMatchObject({ status: 'loading', transcriptLoading: true, ids: [] })
+    expect(renders[0]).toMatchObject({
+      status: 'loading',
+      transcriptLoading: true,
+      ids: ['a-1']
+    })
+    // Every commit of the window, not just the first: the re-subscribe lands a
+    // commit after it, so clearing the cache there blanks the transcript the
+    // user actually sees while leaving a first-frame assertion green.
+    expect([...new Set(renders.map((entry) => entry.ids.join(',')))]).toEqual(['a-1'])
+
+    // The fresh client's snapshot supersedes the held list.
+    await act(async () =>
+      emitFresh({ type: 'snapshot', messages: [message('a-1'), message('a-2')], hasMore: false })
+    )
+    expect(renders.at(-1)).toMatchObject({
+      status: 'ready',
+      transcriptLoading: false,
+      ids: ['a-1', 'a-2']
+    })
+  })
+
+  it('never holds a cached list across a host/workspace source change', async () => {
+    const firstClient = {
+      subscribe: vi.fn((_method: string, _params: unknown, onData: (frame: unknown) => void) => {
+        onData({ type: 'snapshot', messages: [message('source-a')], hasMore: false })
+        return () => {}
+      })
+    } as unknown as RpcClient
+    await mountAt(firstClient, 'session-a')
+
+    const secondClient = { subscribe: vi.fn(() => () => {}) } as unknown as RpcClient
+    renders.length = 0
+    await act(async () =>
+      renderer?.update(
+        createElement(Harness, {
+          client: secondClient,
+          sessionId: 'session-a',
+          sourceIdentity: 'host-b\0workspace-b'
+        })
+      )
+    )
+
+    expect(renders[0]).toMatchObject({ status: 'loading', ids: [] })
   })
 
   it('never hands out the previous session’s messages under the new session id', async () => {
diff --git a/mobile/src/session/use-mobile-native-chat-session.ts b/mobile/src/session/use-mobile-native-chat-session.ts
index 56db7def5..6305d0418 100644
--- a/mobile/src/session/use-mobile-native-chat-session.ts
+++ b/mobile/src/session/use-mobile-native-chat-session.ts
@@ -1,4 +1,8 @@
 import { useCallback, useEffect, useRef, useState } from 'react'
+import {
+  createNativeChatTranscriptRetention,
+  encodeNativeChatTranscriptIdentity
+} from '../../../src/shared/native-chat-transcript-retention'
 import type { NativeChatMessage } from '../../../src/shared/native-chat-types'
 import { buildNativeChatSubscriptionId } from '../../../src/shared/native-chat-stream-unsubscribe'
 import type { RpcClient } from '../transport/rpc-client'
@@ -28,9 +32,6 @@ export type MobileNativeChatSession = {
   loadEarlier: () => void
 }
 
-// Stable empty reference so a not-yet-current read doesn't churn consumers.
-const EMPTY_MESSAGES: NativeChatMessage[] = []
-
 // Small first page for a fast first paint; grows by a page as the user scrolls.
 const INITIAL_LIMIT = 40
 const PAGE = 60
@@ -45,13 +46,20 @@ type ReadSessionResult =
  *  an ordered tail); live appends merge by id so order stays stable. */
 export function useMobileNativeChatSession(args: {
   client: RpcClient | null
+  /** Stable host/workspace source; unlike `client`, it survives manual reconnect. */
+  sourceIdentity: string
   agent: string | null
   sessionId: string | null
   transcriptPath: string | null
 }): MobileNativeChatSession {
-  const { client, agent, sessionId, transcriptPath } = args
+  const { client, sourceIdentity, agent, sessionId, transcriptPath } = args
   const [messages, setMessages] = useState<NativeChatMessage[]>([])
-  const identity = `${agent ?? ''}\0${sessionId ?? ''}\0${transcriptPath ?? ''}`
+  const identity = encodeNativeChatTranscriptIdentity([
+    sourceIdentity,
+    agent,
+    sessionId,
+    transcriptPath
+  ])
   // Pre-read status is a pure function of the props, so derive it rather than
   // letting the effect write it a commit later.
   const initialStatus: MobileNativeChatStatus =
@@ -95,6 +103,13 @@ export function useMobileNativeChatSession(args: {
   // Whether this subscription already delivered its base snapshot; later
   // snapshots on the same subscription are reconnect replays, not fresh bases.
   const snapshotSeenRef = useRef(false)
+  const transcriptRetentionRef = useRef(createNativeChatTranscriptRetention())
+  const settledReady = settled?.status === 'ready'
+  useEffect(() => {
+    if (settledReady) {
+      transcriptRetentionRef.current.capture(identity, messages)
+    }
+  }, [identity, messages, settledReady])
 
   // Replace the base list (read results are an ordered tail). Resets the merger
   // cache so the index is rebuilt once over the new base.
@@ -258,10 +273,17 @@ export function useMobileNativeChatSession(args: {
     })()
   }, [client, agent, sessionId, transcriptPath, hasMore, setList])
 
+  const visibleMessages = transcriptRetentionRef.current.visible({
+    identity,
+    messages,
+    settled: settledReady,
+    loading: status === 'loading'
+  })
+
   return {
     // Withheld until the settled read belongs to this identity: the effect that
     // clears the previous tab's list is passive, so `messages` lags a commit.
-    messages: settled ? messages : EMPTY_MESSAGES,
+    messages: visibleMessages,
     status,
     transcriptLoading: status === 'loading',
     error,
diff --git a/src/renderer/src/components/native-chat/NativeChatInteractiveCard.test.tsx b/src/renderer/src/components/native-chat/NativeChatInteractiveCard.test.tsx
index a9b65f950..7f5c41034 100644
--- a/src/renderer/src/components/native-chat/NativeChatInteractiveCard.test.tsx
+++ b/src/renderer/src/components/native-chat/NativeChatInteractiveCard.test.tsx
@@ -48,13 +48,15 @@ function renderCard(canSend = true): ReturnType<typeof render> {
 function cardElement(
   canSend = true,
   messages?: readonly NativeChatMessage[],
-  onShowingQuestionChange?: (showing: boolean) => void
+  onShowingQuestionChange?: (showing: boolean) => void,
+  transcriptSettled = true
 ): React.JSX.Element {
   return (
     <NativeChatInteractiveCard
       paneKey="tab-1:leaf-1"
       canSend={canSend}
       messages={messages}
+      transcriptSettled={transcriptSettled}
       onShowingQuestionChange={onShowingQuestionChange}
       send={{
         sendAnswer: mocks.sendAnswer,
@@ -233,6 +235,12 @@ describe('NativeChatInteractiveCard transcript fallback', () => {
     expect(onShowingQuestionChange).toHaveBeenCalledWith(true)
   })
 
+  it('withholds a retained transcript ask while its replacement read is unsettled', () => {
+    render(cardElement(true, [askCallMessage('Stale transcript question?')], undefined, false))
+
+    expect(screen.queryByText('Stale transcript question?')).not.toBeInTheDocument()
+  })
+
   it('prefers live status over the transcript when both carry a prompt', () => {
     storeState.agentStatusByPaneKey['tab-1:leaf-1'].interactivePrompt = INITIAL_PROMPT
     render(cardElement(true, [askCallMessage('Stale transcript question?')]))
diff --git a/src/renderer/src/components/native-chat/NativeChatInteractiveCard.tsx b/src/renderer/src/components/native-chat/NativeChatInteractiveCard.tsx
index c02df5c13..0b3e110c0 100644
--- a/src/renderer/src/components/native-chat/NativeChatInteractiveCard.tsx
+++ b/src/renderer/src/components/native-chat/NativeChatInteractiveCard.tsx
@@ -1,6 +1,6 @@
 import { useCallback, useEffect, useLayoutEffect, useMemo, useRef, useState } from 'react'
 import { useAppStore } from '../../store'
-import { extractPendingAsk } from '../../../../shared/native-chat-ask'
+import { resolveNativeChatAsk } from '../../../../shared/native-chat-ask'
 import type { NativeChatMessage } from '../../../../shared/native-chat-types'
 import { parseInteractivePrompt } from './native-chat-interactive-prompt'
 import { nativeChatCardDismissKey } from './native-chat-dismiss-key'
@@ -33,6 +33,7 @@ export function NativeChatInteractiveCard({
   send,
   canSend,
   messages,
+  transcriptSettled,
   onShowingQuestionChange,
   answerInputRef
 }: {
@@ -42,6 +43,7 @@ export function NativeChatInteractiveCard({
   /** Transcript to fall back on when live status carries no prompt. Pass the
    *  command-boundary-trimmed messages so an ask abandoned via `/clear` stays gone. */
   messages?: readonly NativeChatMessage[]
+  transcriptSettled: boolean
   /** Reports whether a question card is on screen so the view can replace the
    *  composer with it (the card's free-text row is the answer input). */
   onShowingQuestionChange?: (showing: boolean) => void
@@ -59,12 +61,16 @@ export function NativeChatInteractiveCard({
 
   const card = useMemo(() => {
     const statusCard = parseInteractivePrompt(interactivePrompt, interactiveToolName ?? undefined)
-    if (statusCard || !messages) {
+    if (statusCard?.kind === 'approval') {
       return statusCard
     }
-    const prompt = extractPendingAsk(messages)
+    const prompt = resolveNativeChatAsk({
+      liveAsk: statusCard?.prompt ?? null,
+      messages: messages ?? [],
+      transcriptSettled: transcriptSettled && messages != null
+    })
     return prompt ? { kind: 'question' as const, prompt } : null
-  }, [interactivePrompt, interactiveToolName, messages])
+  }, [interactivePrompt, interactiveToolName, messages, transcriptSettled])
   const cardKey = useMemo(() => nativeChatCardDismissKey(card), [card])
   const [dismissedKey, setDismissedKey] = useState<string | null>(null)
   // A question answer is a paced multi-step write (body→Enter per question); keep
diff --git a/src/renderer/src/components/native-chat/NativeChatView.tsx b/src/renderer/src/components/native-chat/NativeChatView.tsx
index 33a8ddecb..2fb458166 100644
--- a/src/renderer/src/components/native-chat/NativeChatView.tsx
+++ b/src/renderer/src/components/native-chat/NativeChatView.tsx
@@ -3,7 +3,7 @@ import { useShallow } from 'zustand/react/shallow'
 import { useAppStore } from '../../store'
 import { useNativeChatLaunchDraftSignal } from './use-native-chat-launch-draft-adoption'
 import type { NativeChatSession } from '../../../../shared/native-chat-types'
-import { useNativeChatLiveSession } from './use-native-chat-live-session'
+import { useNativeChatRetainedSession } from './use-native-chat-retained-session'
 import { selectNativeChatViewState } from './native-chat-view-state'
 import { NativeChatMessageList } from './NativeChatMessageList'
 import { NativeChatComposer, type NativeChatComposerHandle } from './NativeChatComposer'
@@ -131,7 +131,7 @@ function NativeChatResolvedView({
   const runtimeEnvironmentId = useAppStore((s) =>
     selectNativeChatRuntimeEnvironmentId(s, terminalTabId)
   )
-  const session = useNativeChatLiveSession({
+  const session = useNativeChatRetainedSession({
     paneKey,
     agent,
     sessionId,
@@ -430,6 +430,7 @@ function NativeChatResolvedView({
         send={interactiveSend}
         canSend={canSend}
         messages={sessionAfterCommandBoundaries.messages}
+        transcriptSettled={session.readPhase === 'ready'}
         onShowingQuestionChange={setQuestionActive}
         answerInputRef={questionAnswerInputRef}
       />
diff --git a/src/renderer/src/components/native-chat/use-native-chat-retained-session.test.ts b/src/renderer/src/components/native-chat/use-native-chat-retained-session.test.ts
new file mode 100644
index 000000000..17b5801b0
--- /dev/null
+++ b/src/renderer/src/components/native-chat/use-native-chat-retained-session.test.ts
@@ -0,0 +1,102 @@
+// @vitest-environment happy-dom
+
+import { act, createElement } from 'react'
+import { createRoot, type Root } from 'react-dom/client'
+import { afterEach, describe, expect, it, vi } from 'vitest'
+import type { NativeChatMessage } from '../../../../shared/native-chat-types'
+import type {
+  NativeChatLiveSession,
+  UseNativeChatLiveSessionArgs
+} from './use-native-chat-live-session'
+
+const { liveSession } = vi.hoisted(() => ({ liveSession: vi.fn() }))
+
+vi.mock('./use-native-chat-live-session', () => ({ useNativeChatLiveSession: liveSession }))
+
+import { useNativeChatRetainedSession } from './use-native-chat-retained-session'
+
+const ARGS: UseNativeChatLiveSessionArgs = {
+  paneKey: 'tab:leaf',
+  agent: 'claude',
+  sessionId: 'session',
+  runtimeEnvironmentId: 'owner-a'
+}
+
+function message(id: string): NativeChatMessage {
+  return { id, role: 'assistant', blocks: [], timestamp: 0, source: 'transcript' }
+}
+
+function session(
+  readPhase: NativeChatLiveSession['readPhase'],
+  messages: NativeChatMessage[],
+  sessionId: string | null = 'session'
+): NativeChatLiveSession {
+  return {
+    agent: 'claude',
+    sessionId,
+    messages,
+    status: readPhase === 'loading' ? 'loading' : 'ready',
+    hasMore: false,
+    loadingEarlier: false,
+    loadEarlier: vi.fn(),
+    readPhase
+  }
+}
+
+describe('useNativeChatRetainedSession', () => {
+  let root: Root | null = null
+  let latest: NativeChatLiveSession | null = null
+
+  function Probe(props: UseNativeChatLiveSessionArgs): null {
+    latest = useNativeChatRetainedSession(props)
+    return null
+  }
+
+  async function render(props: UseNativeChatLiveSessionArgs): Promise<void> {
+    if (!root) {
+      root = createRoot(document.createElement('div'))
+    }
+    await act(async () => root?.render(createElement(Probe, props)))
+  }
+
+  afterEach(() => {
+    act(() => root?.unmount())
+    root = null
+    latest = null
+    liveSession.mockReset()
+  })
+
+  it('keeps settled messages during a same-identity rebind', async () => {
+    liveSession.mockReturnValue(session('ready', [message('settled')]))
+    await render(ARGS)
+
+    liveSession.mockReturnValue(session('loading', []))
+    await render(ARGS)
+
+    expect(latest?.readPhase).toBe('loading')
+    expect(latest?.messages.map((entry) => entry.id)).toEqual(['settled'])
+  })
+
+  it('misses retained messages when the source owner changes', async () => {
+    liveSession.mockReturnValue(session('ready', [message('owner-a')]))
+    await render(ARGS)
+
+    liveSession.mockReturnValue(session('loading', []))
+    await render({ ...ARGS, runtimeEnvironmentId: 'owner-b' })
+
+    expect(latest?.readPhase).toBe('loading')
+    expect(latest?.messages).toEqual([])
+  })
+
+  it('does not overwrite retention with the session-less view', async () => {
+    liveSession.mockReturnValue(session('ready', [message('settled')]))
+    await render(ARGS)
+
+    liveSession.mockReturnValue(session('ready', [], null))
+    await render({ ...ARGS, sessionId: null })
+    liveSession.mockReturnValue(session('loading', []))
+    await render(ARGS)
+
+    expect(latest?.messages.map((entry) => entry.id)).toEqual(['settled'])
+  })
+})
diff --git a/src/renderer/src/components/native-chat/use-native-chat-retained-session.ts b/src/renderer/src/components/native-chat/use-native-chat-retained-session.ts
new file mode 100644
index 000000000..e10ccecf5
--- /dev/null
+++ b/src/renderer/src/components/native-chat/use-native-chat-retained-session.ts
@@ -0,0 +1,53 @@
+import { useEffect, useRef } from 'react'
+import {
+  createNativeChatTranscriptRetention,
+  encodeNativeChatTranscriptIdentity
+} from '../../../../shared/native-chat-transcript-retention'
+import {
+  useNativeChatLiveSession,
+  type NativeChatLiveSession,
+  type UseNativeChatLiveSessionArgs
+} from './use-native-chat-live-session'
+
+/** Keeps one committed conversation visible while its exact source rebinds. */
+export function useNativeChatRetainedSession(
+  args: UseNativeChatLiveSessionArgs
+): NativeChatLiveSession {
+  const session = useNativeChatLiveSession(args)
+  const identity = encodeNativeChatTranscriptIdentity([
+    args.paneKey,
+    args.runtimeEnvironmentId ?? null,
+    args.agent,
+    args.sessionId,
+    args.transcriptPath ?? null
+  ])
+  const activeIdentityRef = useRef(identity)
+  const retentionRef = useRef(createNativeChatTranscriptRetention())
+  const sessionMatchesIdentity = activeIdentityRef.current === identity
+  const readPhase = sessionMatchesIdentity ? session.readPhase : 'loading'
+
+  useEffect(() => {
+    activeIdentityRef.current = identity
+  }, [identity])
+  useEffect(() => {
+    if (sessionMatchesIdentity && args.sessionId !== null && session.readPhase === 'ready') {
+      retentionRef.current.capture(identity, session.messages)
+    }
+  }, [args.sessionId, identity, session.messages, session.readPhase, sessionMatchesIdentity])
+
+  const messages = retentionRef.current.visible({
+    identity,
+    messages: session.messages,
+    settled: readPhase === 'ready',
+    loading: readPhase === 'loading'
+  })
+  if (messages === session.messages && readPhase === session.readPhase) {
+    return session
+  }
+  return {
+    ...session,
+    messages,
+    readPhase,
+    ...(sessionMatchesIdentity ? {} : { status: 'loading' as const, error: undefined })
+  }
+}
diff --git a/src/shared/native-chat-ask.test.ts b/src/shared/native-chat-ask.test.ts
index 4cdad0148..292209671 100644
--- a/src/shared/native-chat-ask.test.ts
+++ b/src/shared/native-chat-ask.test.ts
@@ -4,7 +4,12 @@ import {
   type NativeChatBlock,
   type NativeChatMessage
 } from './native-chat-types'
-import { extractPendingAsk, nativeChatAskDismissKey, parseAskFromStatus } from './native-chat-ask'
+import {
+  extractPendingAsk,
+  nativeChatAskDismissKey,
+  parseAskFromStatus,
+  resolveNativeChatAsk
+} from './native-chat-ask'
 
 function message(id: string, blocks: NativeChatBlock[]): NativeChatMessage {
   return { id, role: 'assistant', blocks, timestamp: 1, source: 'transcript' }
@@ -178,3 +183,23 @@ describe('parseAskFromStatus', () => {
     expect(prompt?.questions[0]?.options.map((o) => o.label)).toEqual(['a', 'b'])
   })
 })
+
+describe('resolveNativeChatAsk', () => {
+  const transcript = [message('m1', [call('AskUserQuestion', QUESTIONS_INPUT)])]
+
+  it('withholds transcript state until the read settles', () => {
+    expect(
+      resolveNativeChatAsk({ liveAsk: null, messages: transcript, transcriptSettled: false })
+    ).toBeNull()
+    expect(
+      resolveNativeChatAsk({ liveAsk: null, messages: transcript, transcriptSettled: true })
+    )?.toMatchObject(QUESTIONS_INPUT)
+  })
+
+  it('keeps a live ask authoritative while transcript history is unsettled', () => {
+    const liveAsk = { questions: [{ question: 'Live?', options: [], multiSelect: false }] }
+    expect(resolveNativeChatAsk({ liveAsk, messages: transcript, transcriptSettled: false })).toBe(
+      liveAsk
+    )
+  })
+})
diff --git a/src/shared/native-chat-ask.ts b/src/shared/native-chat-ask.ts
index 1a37cedf3..5b21520fd 100644
--- a/src/shared/native-chat-ask.ts
+++ b/src/shared/native-chat-ask.ts
@@ -131,6 +131,15 @@ export function extractPendingAsk(messages: readonly NativeChatMessage[]): AskPr
   return pending
 }
 
+/** Prefers live status and consults transcript history only after its read settles. */
+export function resolveNativeChatAsk(args: {
+  liveAsk: AskPrompt | null
+  messages: readonly NativeChatMessage[]
+  transcriptSettled: boolean
+}): AskPrompt | null {
+  return args.liveAsk ?? (args.transcriptSettled ? extractPendingAsk(args.messages) : null)
+}
+
 /** One question's chosen answer, normalized for delivery: the selected option
  *  indices (in option order) plus any free-text "other" answer. Index-based (not
  *  label text) so the answer can be delivered by the selector's stable option
diff --git a/src/shared/native-chat-transcript-retention.test.ts b/src/shared/native-chat-transcript-retention.test.ts
new file mode 100644
index 000000000..e62d980bd
--- /dev/null
+++ b/src/shared/native-chat-transcript-retention.test.ts
@@ -0,0 +1,54 @@
+import { describe, expect, it } from 'vitest'
+import type { NativeChatMessage } from './native-chat-types'
+import {
+  createNativeChatTranscriptRetention,
+  encodeNativeChatTranscriptIdentity
+} from './native-chat-transcript-retention'
+
+function message(id: string): NativeChatMessage {
+  return { id, role: 'assistant', blocks: [], timestamp: 0, source: 'transcript' }
+}
+
+describe('native chat transcript retention', () => {
+  it('holds only the latest settled transcript for the same identity while loading', () => {
+    const retention = createNativeChatTranscriptRetention()
+    const first = [message('first')]
+    const second = [message('second')]
+
+    retention.capture('source-a', first)
+    expect(
+      retention.visible({ identity: 'source-a', messages: [], settled: false, loading: true })
+    ).toBe(first)
+    expect(
+      retention.visible({ identity: 'source-b', messages: [], settled: false, loading: true })
+    ).toEqual([])
+
+    retention.capture('source-b', second)
+    expect(
+      retention.visible({ identity: 'source-a', messages: [], settled: false, loading: true })
+    ).toEqual([])
+    expect(
+      retention.visible({ identity: 'source-b', messages: [], settled: false, loading: true })
+    ).toBe(second)
+  })
+
+  it('never substitutes retained history for a settled or non-loading read', () => {
+    const retention = createNativeChatTranscriptRetention()
+    const retained = [message('retained')]
+    const fresh = [message('fresh')]
+    retention.capture('source', retained)
+
+    expect(
+      retention.visible({ identity: 'source', messages: fresh, settled: true, loading: false })
+    ).toBe(fresh)
+    expect(
+      retention.visible({ identity: 'source', messages: [], settled: false, loading: false })
+    ).toEqual([])
+  })
+
+  it('encodes identity components without delimiter collisions', () => {
+    expect(encodeNativeChatTranscriptIdentity(['host\0workspace', 'session'])).not.toBe(
+      encodeNativeChatTranscriptIdentity(['host', 'workspace\0session'])
+    )
+  })
+})
diff --git a/src/shared/native-chat-transcript-retention.ts b/src/shared/native-chat-transcript-retention.ts
new file mode 100644
index 000000000..a2f891bb7
--- /dev/null
+++ b/src/shared/native-chat-transcript-retention.ts
@@ -0,0 +1,36 @@
+import type { NativeChatMessage } from './native-chat-types'
+
+export const EMPTY_NATIVE_CHAT_TRANSCRIPT: NativeChatMessage[] = []
+
+export function encodeNativeChatTranscriptIdentity(parts: readonly (string | null)[]): string {
+  return JSON.stringify(parts)
+}
+
+export type NativeChatTranscriptRetention = {
+  capture: (identity: string, messages: NativeChatMessage[]) => void
+  visible: (args: {
+    identity: string
+    messages: NativeChatMessage[]
+    settled: boolean
+    loading: boolean
+  }) => NativeChatMessage[]
+}
+
+/** Retains one settled transcript so a same-source rebind does not blank the conversation. */
+export function createNativeChatTranscriptRetention(): NativeChatTranscriptRetention {
+  let captured: { identity: string; messages: NativeChatMessage[] } | null = null
+
+  return {
+    capture(identity, messages) {
+      captured = { identity, messages }
+    },
+    visible({ identity, messages, settled, loading }) {
+      if (settled) {
+        return messages
+      }
+      return loading && captured?.identity === identity
+        ? captured.messages
+        : EMPTY_NATIVE_CHAT_TRANSCRIPT
+    }
+  }
+}