fix(native-chat): rotate immediately rejected retries

src/renderer/src/components/native-chat/use-structured-agent-session-outbox.test.tsx

@@ -643,7 +643,7 @@ describe('useStructuredAgentSessionOutbox', () => {
           11
         )
       )
-    const { result, rerender } = renderHook(
+    const { result } = renderHook(
       ({ submissions }: { submissions: readonly AgentJournalSubmission[] }) =>
         useStructuredAgentSessionOutbox({
           sessionId: 'session-1',
@@ -669,7 +669,7 @@ describe('useStructuredAgentSessionOutbox', () => {
     expect(result.current.outbox[0]?.state).toBe('queued')
     expect(result.current.blockedClientMessageId).toBe(firstId)
 
-    rerender({ submissions: [writeFailed(firstId)] })
+    // Retry immediately, before the journal subscription can publish the rejected row.
     act(() => result.current.retry(firstId))
     await waitFor(() => expect(result.current.outbox).toHaveLength(0))
 

src/renderer/src/components/native-chat/use-structured-agent-session-outbox.ts

@@ -52,6 +52,7 @@ export function useStructuredAgentSessionOutbox(args: {
   const dispatchingRef = useRef(false)
   const dispatchGenerationRef = useRef(0)
   const blockedIdRef = useRef<string | null>(null)
+  const retryWithFreshClientMessageIdRef = useRef<string | null>(null)
   const probeAttemptsRef = useRef({ id: null as string | null, attempts: 0 })
   const [error, setError] = useState<string | null>(null)
   const [errorSession, setErrorSession] = useState(sessionId)
@@ -70,6 +71,7 @@ export function useStructuredAgentSessionOutbox(args: {
     dispatchGenerationRef.current += 1
     dispatchingRef.current = false
     blockedIdRef.current = null
+    retryWithFreshClientMessageIdRef.current = null
     probeAttemptsRef.current = { id: null, attempts: 0 }
   }, [fence, sessionId, targetKey])
 
@@ -125,6 +127,7 @@ export function useStructuredAgentSessionOutbox(args: {
   const applyDisposition = useCallback(
     (disposition: StructuredAgentSessionSendDisposition): void => {
       blockedIdRef.current = disposition.blockedClientMessageId
+      retryWithFreshClientMessageIdRef.current = disposition.retryWithFreshClientMessageId
       setError(disposition.error)
       outboxRef.current = disposition.entries
       setOutbox(disposition.entries)
@@ -275,7 +278,12 @@ export function useStructuredAgentSessionOutbox(args: {
     // A provider-history reconciliation can settle an earlier unknown as
     // rejected before the user presses Retry. Reusing that operation id only
     // replays the settled rejection forever, so rotate the id for a safe resend.
-    if (current && submission?.dispatchState === 'rejected') {
+    if (
+      current &&
+      (submission?.dispatchState === 'rejected' ||
+        retryWithFreshClientMessageIdRef.current === clientMessageId)
+    ) {
+      retryWithFreshClientMessageIdRef.current = null
       const rotated = outboxRef.current.map((entry) =>
         entry.clientMessageId === clientMessageId
           ? {

src/shared/structured-agent-session-send-disposition.ts

@@ -24,6 +24,8 @@ export type StructuredAgentSessionSendDisposition = {
   /** The entry the queue is stuck on, or null when nothing blocks it. Always the
    *  next value, never "unchanged": the caller assigns it verbatim. */
   blockedClientMessageId: string | null
+  /** A rejected result arrived before the journal snapshot; Retry must rotate this id. */
+  retryWithFreshClientMessageId: string | null
 }
 
 type SendDispositionInput = {
@@ -118,7 +120,8 @@ export function disposeStructuredAgentSessionSendResult(
     return {
       entries,
       error: result.refusal.message,
-      blockedClientMessageId: entries[0]?.clientMessageId ?? null
+      blockedClientMessageId: entries[0]?.clientMessageId ?? null,
+      retryWithFreshClientMessageId: null
     }
   }
   const submission = result.value.submission
@@ -126,21 +129,24 @@ export function disposeStructuredAgentSessionSendResult(
     return {
       entries: dropEntry(input),
       error: 'Message delivery is unconfirmed and Orca will not send it again',
-      blockedClientMessageId: input.blockedClientMessageId
+      blockedClientMessageId: input.blockedClientMessageId,
+      retryWithFreshClientMessageId: null
     }
   }
   if (submission.dispatchState === 'accepted') {
     return {
       entries: dropEntry(input),
       error: null,
-      blockedClientMessageId: input.blockedClientMessageId
+      blockedClientMessageId: input.blockedClientMessageId,
+      retryWithFreshClientMessageId: null
     }
   }
   if (submission.dispatchState === 'rejected') {
     return {
       entries: replaceEntryState(input, 'queued'),
       error: rejectionNotice(submission.reason),
-      blockedClientMessageId: input.entry.clientMessageId
+      blockedClientMessageId: input.entry.clientMessageId,
+      retryWithFreshClientMessageId: input.entry.clientMessageId
     }
   }
   // `pending` is the host saying the message was written and is awaiting the
@@ -153,7 +159,8 @@ export function disposeStructuredAgentSessionSendResult(
       submission.dispatchState === 'unknown' ? 'unconfirmed' : 'dispatching'
     ),
     error: null,
-    blockedClientMessageId: input.blockedClientMessageId
+    blockedClientMessageId: input.blockedClientMessageId,
+    retryWithFreshClientMessageId: null
   }
 }
 
@@ -170,6 +177,7 @@ export function disposeStructuredAgentSessionSendFailure(
     error: deliveryUnknown ? 'Message delivery is unconfirmed' : String(input.cause),
     blockedClientMessageId: deliveryUnknown
       ? input.blockedClientMessageId
-      : input.entry.clientMessageId
+      : input.entry.clientMessageId,
+    retryWithFreshClientMessageId: null
   }
 }