diff --git a/mobile/src/session/mobile-structured-send-delivery.test.ts b/mobile/src/session/mobile-structured-send-delivery.test.ts
index 6305bf75df57..8431e32a7aa9 100644
--- a/mobile/src/session/mobile-structured-send-delivery.test.ts
+++ b/mobile/src/session/mobile-structured-send-delivery.test.ts
@@ -169,7 +169,9 @@ describe('mobileStructuredSendDelivery', () => {
     })
   })
 
-  it('never releases an ambiguous id on a later RPC refusal or failure', () => {
+  it('spends an ambiguous id the host has expired, and says to check the chat', () => {
+    // The host refuses an expired id on every replay; keeping it would refuse this text forever.
+    // The earlier attempt may still be in the chat, so the words never say it was not sent.
     expect(
       mobileStructuredSendDelivery(
         {
@@ -179,7 +181,25 @@ describe('mobileStructuredSendDelivery', () => {
         },
         true
       )
-    ).toEqual({ outcome: 'rejected', operationIdSpent: false, error: 'Operation expired' })
+    ).toEqual({
+      outcome: 'rejected',
+      operationIdSpent: true,
+      error:
+        "Orca couldn't confirm your message reached the agent. Check the chat, then send it again if needed."
+    })
+  })
+
+  it('never releases an ambiguous id on any other later RPC refusal or failure', () => {
+    expect(
+      mobileStructuredSendDelivery(
+        {
+          status: 'refused',
+          code: 'agent_session_operation_conflict',
+          message: 'Operation conflict'
+        },
+        true
+      )
+    ).toEqual({ outcome: 'rejected', operationIdSpent: false, error: 'Operation conflict' })
     expect(
       mobileStructuredSendDelivery(
         { status: 'failed', message: 'Your message was not sent. Send it again.' },
diff --git a/mobile/src/session/mobile-structured-send-delivery.ts b/mobile/src/session/mobile-structured-send-delivery.ts
index 466a0d29ff8a..f20dc0971887 100644
--- a/mobile/src/session/mobile-structured-send-delivery.ts
+++ b/mobile/src/session/mobile-structured-send-delivery.ts
@@ -15,11 +15,11 @@
 //     message is a new message and must carry a new id.
 //   rejected — a terminal refusal or rejected submission spends a fresh id. A
 //     pending-admission refusal, or any refusal after earlier transport doubt,
-//     keeps it because neither proves a retained delivery did not happen. The
-//     one exception is a host that refuses the replay's request shape itself
-//     (an older host's strict schema turning `delivery` away): that host can
-//     never accept the replay, so keeping the id would only refuse every later
-//     send of the same text.
+//     keeps it because neither proves a retained delivery did not happen. Two
+//     exceptions spend it anyway, because the host can never accept the replay
+//     and keeping the id would only refuse every later send of the same text:
+//     a host that refuses the replay's request shape itself (an older host's
+//     strict schema turning `delivery` away), and an id the host has expired.
 //   unknown — the one answer that KEEPS its id, whether it came from the host or
 //     from an ack-loss on the way back. The message may be with the provider, so
 //     the retry has to stay a replay. Rotating here is what sent one message to a
@@ -28,6 +28,7 @@
 import type { AgentJournalSubmission } from '../../../src/shared/agent-session-journal-types'
 import type { AgentSessionSendResult } from '../../../src/shared/agent-session-wire'
 import { agentSessionRefusalOperationState } from '../../../src/shared/agent-session-refusal-retry'
+import { agentSessionWriteNoticeEnglish } from '../../../src/shared/agent-session-refusal-notice'
 import { structuredAgentSessionRejectionNotice } from '../../../src/shared/structured-agent-session-send-disposition'
 import type { MobileNativeChatSendOutcome } from './mobile-native-chat-send'
 import type { StructuredAgentSessionMutationCallResult } from './mobile-structured-agent-session-rpc'
@@ -52,6 +53,15 @@ export function mobileStructuredSendDelivery(
     if (refusalState === 'unknown') {
       return { outcome: 'unknown', operationIdSpent: false, error: null }
     }
+    if (retained && result.code === 'agent_session_operation_expired') {
+      // The host refuses this id for good once its day is up, so keeping it would refuse this text
+      // forever. The earlier attempt may already be in the chat, so the words say to check first.
+      return {
+        outcome: 'rejected',
+        operationIdSpent: true,
+        error: agentSessionWriteNoticeEnglish(['sendOutcomeLost'])
+      }
+    }
     return {
       outcome: 'rejected',
       operationIdSpent: refusalState === 'settled-rejected' && !retained,
diff --git a/mobile/src/session/use-mobile-native-chat-drafts.test.ts b/mobile/src/session/use-mobile-native-chat-drafts.test.ts
index 2547d9191bec..a693069dd8c7 100644
--- a/mobile/src/session/use-mobile-native-chat-drafts.test.ts
+++ b/mobile/src/session/use-mobile-native-chat-drafts.test.ts
@@ -142,7 +142,7 @@ describe('useMobileNativeChatDrafts', () => {
     expect(state?.composerText).toBe('ping')
   })
 
-  it('does not clobber newer edits when restoring a rejected send', async () => {
+  it('appends a rejected send after edits typed while it was in flight', async () => {
     await mount('a')
     act(() => state?.setComposerText('ping'))
     const origin = state?.captureSendOrigin('ping')
@@ -157,10 +157,10 @@ describe('useMobileNativeChatDrafts', () => {
         state?.restoreRejectedDraft(origin, 'ping')
       }
     })
-    expect(state?.composerText).toBe('newer edit')
+    expect(state?.composerText).toBe('newer edit\n\nping')
   })
 
-  it('preserves an intentional clear after a newer edit while a rejection is pending', async () => {
+  it('returns a rejected send even after a newer edit was cleared', async () => {
     await mount('a')
     act(() => state?.setComposerText('ping'))
     const origin = state?.captureSendOrigin('ping')
@@ -177,7 +177,7 @@ describe('useMobileNativeChatDrafts', () => {
       }
     })
 
-    expect(state?.composerText).toBe('')
+    expect(state?.composerText).toBe('ping')
   })
 
   it('restores a rejected send onto its originating tab only', async () => {
diff --git a/mobile/src/session/use-mobile-native-chat-drafts.ts b/mobile/src/session/use-mobile-native-chat-drafts.ts
index f17e1826a679..027e6a9a1d89 100644
--- a/mobile/src/session/use-mobile-native-chat-drafts.ts
+++ b/mobile/src/session/use-mobile-native-chat-drafts.ts
@@ -8,6 +8,7 @@ import {
   type SetStateAction
 } from 'react'
 import type { NativeChatMessage } from '../../../src/shared/native-chat-types'
+import { appendReturnedDraftText } from '../../../src/shared/returned-draft-text'
 import {
   countUserTextOccurrences,
   findLandedImagePreviewEchoes,
@@ -77,7 +78,7 @@ export function useMobileNativeChatDrafts(args: {
   readSeededLaunchDraftSeed: () => MobileNativeChatLaunchDraftSeed | null
   /** Clear the composer at send time, before the RPC settles. */
   clearDraftForSend: (origin: MobileNativeChatSendOrigin, text: string) => void
-  /** Put the text back after a definite rejection, unless newer edits exist. */
+  /** Put the text back after a definite rejection, after whatever the composer holds now. */
   restoreRejectedDraft: (origin: MobileNativeChatSendOrigin, text: string) => void
   acceptSend: (origin: MobileNativeChatSendOrigin, text: string, images?: string[]) => void
   holdUnconfirmedSend: (
@@ -200,13 +201,12 @@ export function useMobileNativeChatDrafts(args: {
   }, [])
 
   const restoreRejectedDraft = useCallback((origin: MobileNativeChatSendOrigin, text: string) => {
-    // Why: never clobber text the user typed while the rejection was in flight.
-    setDrafts((previous) =>
-      draftEditGenerationsRef.current.isCurrent(origin.draftKey, origin.draftEditGeneration) &&
-      (previous[origin.draftKey] ?? '') === ''
-        ? { ...previous, [origin.draftKey]: text }
-        : previous
-    )
+    // Appended, so typing done while the send was in flight stays and the returned text isn't dropped.
+    setDrafts((previous) => {
+      const current = previous[origin.draftKey] ?? ''
+      const next = appendReturnedDraftText(current, text)
+      return next === current ? previous : { ...previous, [origin.draftKey]: next }
+    })
   }, [])
 
   const acceptSend = useCallback(
diff --git a/mobile/src/session/use-mobile-structured-agent-session-send.test.tsx b/mobile/src/session/use-mobile-structured-agent-session-send.test.tsx
index 34b66f1dd1fc..086482537ef2 100644
--- a/mobile/src/session/use-mobile-structured-agent-session-send.test.tsx
+++ b/mobile/src/session/use-mobile-structured-agent-session-send.test.tsx
@@ -390,7 +390,7 @@ describe('mobile structured send retries', () => {
     expect(calls().every(([, params]) => !('retryUnknown' in (params as object)))).toBe(true)
   })
 
-  it('keeps an ambiguous id after the host replay window expires', async () => {
+  it('sends under a new id once the host has expired an ambiguous one', async () => {
     let attempts = 0
     sendRequest.mockImplementation(async (method) => {
       if (method !== 'agentSession.send') {
@@ -400,6 +400,9 @@ describe('mobile structured send retries', () => {
       if (attempts === 1) {
         throw markRpcDeliveryUnknown(new Error('Connection closed'))
       }
+      if (attempts === 3) {
+        return sendResult('accepted')
+      }
       return ok({
         ok: false,
         refusal: {
@@ -413,11 +416,16 @@ describe('mobile structured send retries', () => {
     await act(async () => {
       expect(await hook!.sendWithOutcome('old ambiguity')).toBe('unknown')
       expect(await hook!.sendWithOutcome('old ambiguity')).toBe('rejected')
-      expect(await hook!.sendWithOutcome('old ambiguity')).toBe('rejected')
+      expect(await hook!.sendWithOutcome('old ambiguity')).toBe('accepted')
     })
 
     expect(calls()).toHaveLength(3)
-    expect(new Set(sentIds()).size).toBe(1)
+    const [first, replay, fresh] = sentIds()
+    expect(replay).toBe(first)
+    expect(fresh).not.toBe(first)
+    expect(onSendError).toHaveBeenCalledWith(
+      "Orca couldn't confirm your message reached the agent. Check the chat, then send it again if needed."
+    )
   })
 
   it('does not retain an id when the action budget expires before dispatch', async () => {
diff --git a/src/renderer/src/components/native-chat/native-chat-draft-cache.ts b/src/renderer/src/components/native-chat/native-chat-draft-cache.ts
index 333ab7a2c50c..7787c97019d8 100644
--- a/src/renderer/src/components/native-chat/native-chat-draft-cache.ts
+++ b/src/renderer/src/components/native-chat/native-chat-draft-cache.ts
@@ -5,6 +5,7 @@ import type { JSONContent } from '@tiptap/react'
 // draft would be lost on every TUI/GUI round-trip. Mirrors the attachment cache
 // so both halves of an unsent message survive toggles and reconnects.
 
+import { appendReturnedDraftText } from '../../../../shared/returned-draft-text'
 import { setBoundedScopeCacheEntry } from './native-chat-composer-scope-cache'
 
 const draftCache = new Map<string, { text: string; document?: JSONContent }>()
@@ -28,10 +29,6 @@ export function writeNativeChatDraftCache(scopeKey: string, draft: string): void
   })
 }
 
-export function appendNativeChatDraftText(draft: string, text: string): string {
-  return draft === '' ? text : `${draft.trimEnd()}\n\n${text}`
-}
-
 // Only a write from outside the composer notifies; its own writes already hold the text.
 const appendListeners = new Map<string, Set<(text: string) => void>>()
 
@@ -42,7 +39,7 @@ export function appendNativeChatDraftCache(scopeKey: string, text: string): void
   }
   writeNativeChatDraftCache(
     scopeKey,
-    appendNativeChatDraftText(readNativeChatDraftCache(scopeKey), text)
+    appendReturnedDraftText(readNativeChatDraftCache(scopeKey), text)
   )
   appendListeners.get(scopeKey)?.forEach((listener) => listener(text))
 }
diff --git a/src/renderer/src/components/native-chat/structured-agent-session-withdrawn-message-restore.test.tsx b/src/renderer/src/components/native-chat/structured-agent-session-withdrawn-message-restore.test.tsx
index 150b520bcd32..404b35133b44 100644
--- a/src/renderer/src/components/native-chat/structured-agent-session-withdrawn-message-restore.test.tsx
+++ b/src/renderer/src/components/native-chat/structured-agent-session-withdrawn-message-restore.test.tsx
@@ -252,11 +252,13 @@ describe('a message the host withdrew at a Stop', () => {
     unsubscribe()
 
     expect(storedAtRestore).toEqual([id])
-    // The drop never reached storage: the next mount gives the text back again rather than losing it.
+    // The drop never reached storage: after a crash, which loses the in-memory draft, the next mount
+    // gives the text back again rather than losing it.
     cleanup()
+    writeNativeChatDraftCache(PANE, '')
     writeOutbox(SESSION, beforeDrop)
     renderOutbox().rerender({ submissions: [withdrawn(id)] })
-    expect(readNativeChatDraftCache(PANE)).toBe('hello\n\nhello')
+    expect(readNativeChatDraftCache(PANE)).toBe('hello')
   })
 
   it('keeps a message refused for any other reason on its Retry, and gives nothing back', async () => {
diff --git a/src/renderer/src/components/native-chat/use-native-chat-draft.ts b/src/renderer/src/components/native-chat/use-native-chat-draft.ts
index 5653c0a77a85..a5b5d99a143d 100644
--- a/src/renderer/src/components/native-chat/use-native-chat-draft.ts
+++ b/src/renderer/src/components/native-chat/use-native-chat-draft.ts
@@ -1,6 +1,6 @@
 import { useCallback, useEffect, useRef, useState } from 'react'
+import { appendReturnedDraftText } from '../../../../shared/returned-draft-text'
 import {
-  appendNativeChatDraftText,
   readNativeChatDraftCache,
   subscribeToNativeChatDraftAppend,
   writeNativeChatDraftCache
@@ -45,7 +45,7 @@ export function useNativeChatDraft(
         pendingAppendRef.current = {
           scopeKey,
           text:
-            pending?.scopeKey === scopeKey ? appendNativeChatDraftText(pending.text, text) : text
+            pending?.scopeKey === scopeKey ? appendReturnedDraftText(pending.text, text) : text
         }
       }),
     [isComposing, scopeKey]
@@ -61,7 +61,7 @@ export function useNativeChatDraft(
         writeNativeChatDraftCache(
           scopeKey,
           pending?.scopeKey === scopeKey
-            ? appendNativeChatDraftText(resolved, pending.text)
+            ? appendReturnedDraftText(resolved, pending.text)
             : resolved
         )
         return resolved
@@ -74,7 +74,7 @@ export function useNativeChatDraft(
     const pending = pendingAppendRef.current
     pendingAppendRef.current = null
     if (pending?.scopeKey === scopeKey) {
-      setDraft((previous) => appendNativeChatDraftText(previous, pending.text))
+      setDraft((previous) => appendReturnedDraftText(previous, pending.text))
     }
   }, [scopeKey, setDraft])
 
diff --git a/src/shared/returned-draft-text.test.ts b/src/shared/returned-draft-text.test.ts
new file mode 100644
index 000000000000..79f27507cde0
--- /dev/null
+++ b/src/shared/returned-draft-text.test.ts
@@ -0,0 +1,23 @@
+import { describe, expect, it } from 'vitest'
+import { appendReturnedDraftText } from './returned-draft-text'
+
+describe('appendReturnedDraftText', () => {
+  it('fills an empty composer with the returned text as it was typed', () => {
+    expect(appendReturnedDraftText('', 'ping  ')).toBe('ping  ')
+    expect(appendReturnedDraftText(' \n', 'ping')).toBe('ping')
+  })
+
+  it('puts the returned text after a draft, a blank line apart', () => {
+    expect(appendReturnedDraftText('newer edit\n', 'ping')).toBe('newer edit\n\nping')
+  })
+
+  it('adds nothing when the draft already ends with that text', () => {
+    expect(appendReturnedDraftText('ping', 'ping')).toBe('ping')
+    expect(appendReturnedDraftText('first\n\nping\n', 'ping ')).toBe('first\n\nping\n')
+    expect(appendReturnedDraftText('ping', '')).toBe('ping')
+  })
+
+  it('still appends text that only ends a line of the draft', () => {
+    expect(appendReturnedDraftText('say ping', 'ping')).toBe('say ping\n\nping')
+  })
+})
diff --git a/src/shared/returned-draft-text.ts b/src/shared/returned-draft-text.ts
new file mode 100644
index 000000000000..4dc67520d7fa
--- /dev/null
+++ b/src/shared/returned-draft-text.ts
@@ -0,0 +1,19 @@
+/**
+ * Puts text a chat handed back after what the composer already holds, a blank line apart. It never
+ * replaces typed text (a whitespace-only draft counts as empty), and adds nothing when the draft
+ * already ends with that text, so handing the same text back twice leaves one copy.
+ */
+export function appendReturnedDraftText(draft: string, text: string): string {
+  const returned = text.trimEnd()
+  if (returned.trim() === '') {
+    return draft
+  }
+  const kept = draft.trimEnd()
+  if (kept === '') {
+    return text
+  }
+  if (kept === returned || kept.endsWith(`\n\n${returned}`)) {
+    return draft
+  }
+  return `${kept}\n\n${text}`
+}