diff --git a/src/renderer/src/components/native-chat/structured-agent-session-outbox-dispatch.ts b/src/renderer/src/components/native-chat/structured-agent-session-outbox-dispatch.ts
index add67964f7d..7b143006b74 100644
--- a/src/renderer/src/components/native-chat/structured-agent-session-outbox-dispatch.ts
+++ b/src/renderer/src/components/native-chat/structured-agent-session-outbox-dispatch.ts
@@ -93,11 +93,13 @@ export function requeueInterruptedStructuredAgentSessionDispatches(
 
 /**
  * Commits a settlement: a message coming back goes to its conversation's draft before its entry
- * leaves the outbox, so a failure between the two repeats the text and never loses it.
+ * ends (which clears the notes it carried) and before it leaves the outbox, so a failure between
+ * them repeats the text and never loses it.
  */
 export function commitStructuredAgentSessionSettledOutbox(
   sessionId: string,
-  settled: StructuredAgentSessionSettledOutbox
+  settled: StructuredAgentSessionSettledOutbox,
+  endEntry: () => void = () => {}
 ): void {
   if (settled.returned) {
     returnStructuredAgentSessionMessage(settled.returned.entry)
@@ -105,6 +107,7 @@ export function commitStructuredAgentSessionSettledOutbox(
       setStructuredAgentSessionChatLine(sessionId, settled.returned.words)
     }
   }
+  endEntry()
   commitStructuredAgentSessionOutbox(sessionId, settled.entries)
 }
 
@@ -154,9 +157,6 @@ export function settleStructuredAgentSessionOutboxEntry(
     return
   }
   const ending = structuredAgentSessionSettlementEnding(settlement)
-  if (ending) {
-    endStructuredAgentSessionEntry(entry, ending)
-  }
   // A send a Stop outran never goes again: no answer leaves it waiting for the Stop's.
   const kept =
     entry.stoppedBy !== undefined && settlement.kind === 'unanswered'
@@ -164,7 +164,12 @@ export function settleStructuredAgentSessionOutboxEntry(
       : settlement
   commitStructuredAgentSessionSettledOutbox(
     sessionId,
-    applyStructuredAgentSessionSendSettlement(current, clientMessageId, kept)
+    applyStructuredAgentSessionSendSettlement(current, clientMessageId, kept),
+    () => {
+      if (ending) {
+        endStructuredAgentSessionEntry(entry, ending)
+      }
+    }
   )
   sayStructuredAgentSessionSettlement(sessionId, clientMessageId, kept)
 }
diff --git a/src/renderer/src/components/native-chat/structured-agent-session-outbox-journal-settlement.ts b/src/renderer/src/components/native-chat/structured-agent-session-outbox-journal-settlement.ts
index f5e6e7438c4..cef54900e17 100644
--- a/src/renderer/src/components/native-chat/structured-agent-session-outbox-journal-settlement.ts
+++ b/src/renderer/src/components/native-chat/structured-agent-session-outbox-journal-settlement.ts
@@ -55,19 +55,20 @@ export function settleStructuredAgentSessionOutboxFromJournal(
   if (entries === current) {
     return entries
   }
-  for (const { entry, settlement } of settled) {
-    const ending = structuredAgentSessionSettlementEnding(settlement)
-    if (ending) {
-      endStructuredAgentSessionEntry(entry, ending)
-    }
-  }
-  // Each returned message goes to the draft before the outbox that drops it is saved.
+  // Each returned message goes to the draft before its entry ends (clearing the notes it carried)
+  // and before the outbox that drops it is saved.
   for (const back of returned) {
     returnStructuredAgentSessionMessage(back.entry)
     if (back.words) {
       setStructuredAgentSessionChatLine(sessionId, back.words)
     }
   }
+  for (const { entry, settlement } of settled) {
+    const ending = structuredAgentSessionSettlementEnding(settlement)
+    if (ending) {
+      endStructuredAgentSessionEntry(entry, ending)
+    }
+  }
   commitStructuredAgentSessionOutbox(sessionId, entries)
   for (const { entry, settlement } of settled) {
     sayStructuredAgentSessionSettlement(sessionId, entry.clientMessageId, settlement)
diff --git a/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.ts b/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.ts
index 7163ae2beb8..2de65d618d5 100644
--- a/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.ts
+++ b/src/renderer/src/components/native-chat/use-structured-agent-session-outbox.ts
@@ -295,8 +295,9 @@ export function useStructuredAgentSessionOutbox(args: {
         return
       }
       for (const entry of next.withdrawn) {
-        endStructuredAgentSessionEntry(entry, 'returned')
+        // The draft holds the text before the notes it carried are cleared.
         returnStructuredAgentSessionMessage(entry)
+        endStructuredAgentSessionEntry(entry, 'returned')
         // Back in the composer, it is no longer being sent, so what the line said about it goes.
         clearStructuredAgentSessionChatLineHeldBy(sessionId, entry.clientMessageId)
       }
diff --git a/src/renderer/src/lib/notes-carried-by-chat.test.ts b/src/renderer/src/lib/notes-carried-by-chat.test.ts
index baf637f0227..d5652ae4123 100644
--- a/src/renderer/src/lib/notes-carried-by-chat.test.ts
+++ b/src/renderer/src/lib/notes-carried-by-chat.test.ts
@@ -224,6 +224,17 @@ function openChat(sessionId: string, fence: number | null = 1) {
   )
 }
 
+/** What the session's draft held each time notes were cleared: the text must already be there,
+ *  so a crash between the two never loses both. */
+function draftWhenNotesClear(sessionId: string): string[] {
+  const seen: string[] = []
+  mocks.clearDeliveredDiffComments.mockImplementation(async () => {
+    seen.push(readNativeChatDraftCache(structuredAgentSessionDraftScopeKey(sessionId)))
+    return true
+  })
+  return seen
+}
+
 /** A store change, as a workspace's notes loading makes. */
 function notifyStore(): void {
   for (const listener of mocks.storeListeners) {
@@ -301,6 +312,7 @@ describe('notes sent to a new agent', () => {
     reload()
     expect(isNoteInFlight(KEY_A)).toBe(true)
 
+    const cleared = draftWhenNotesClear(chat.sessionId)
     openChat(chat.sessionId)
     await waitFor(() => readOutbox(chat.sessionId).length === 0)
     expect(isNoteInFlight(KEY_A)).toBe(false)
@@ -309,6 +321,7 @@ describe('notes sent to a new agent', () => {
     )
     // One owner: the draft holds the text, so the notes leave the shelf.
     expect(mocks.clearDeliveredDiffComments).toHaveBeenCalledExactlyOnceWith(WORKTREE_ID, [NOTE_A])
+    expect(cleared).toEqual([NOTES])
   })
 
   it('stay held while a failed chat keeps them to start again, and leave once it delivers', async () => {
@@ -373,6 +386,7 @@ describe('notes sent to a chat already open', () => {
     })
     expect(isNoteInFlight(KEY_A)).toBe(true)
 
+    const cleared = draftWhenNotesClear(target.sessionId)
     mocks.callStructuredAgentSession.mockResolvedValue(REFUSED)
     openChat(target.sessionId)
     await waitFor(() => readOutbox(target.sessionId).length === 0)
@@ -381,6 +395,7 @@ describe('notes sent to a chat already open', () => {
       NOTES
     )
     expect(mocks.clearDeliveredDiffComments).toHaveBeenCalledExactlyOnceWith(WORKTREE_ID, [NOTE_A])
+    expect(cleared).toEqual([NOTES])
   })
 
   it('are used when a Stop takes back the message before it went out', async () => {
@@ -390,6 +405,7 @@ describe('notes sent to a chat already open', () => {
       target,
       carriedNoteKeys: [KEY_A]
     })
+    const cleared = draftWhenNotesClear(target.sessionId)
     const view = openChat(target.sessionId, null)
     view.result.current.stop('stop-1')
 
@@ -399,6 +415,7 @@ describe('notes sent to a chat already open', () => {
     )
     expect(isNoteInFlight(KEY_A)).toBe(false)
     expect(mocks.clearDeliveredDiffComments).toHaveBeenCalledExactlyOnceWith(WORKTREE_ID, [NOTE_A])
+    expect(cleared).toEqual([NOTES])
   })
 
   it('are cleared once their workspace loads, when the host took the message before that', async () => {