fix(ui): retain first-chat uploads through task creation

Co-Authored-By: Paperclip <noreply@paperclip.ing>

maps/feature-map/agent-chat.md

@@ -39,6 +39,17 @@ Preconditions: follow the [baseline](./README.md#before-driving-a-journey). Enab
 
 Automated: [chat landing](../../ui/src/pages/AgentChats.test.tsx) checks recent-chat routing; [conversation service](../../server/src/__tests__/agent-conversations.test.ts) covers persisted conversation behavior.
 
+Automated: [thread and composer](../../ui/src/components/TaskChatThread.test.tsx)
+keeps an in-flight attachment through first-chat creation on desktop and mobile,
+while initial history for an existing conversation stays deferred. The
+[first-upload browser journey](../../tests/e2e/agent-chat-projects.spec.ts)
+checks the visible file chip, server attachment, no premature agent run, and
+saved reference after send and reload. That journey uses a simulated agent.
+
+Manual: In a conversation with no messages, attach a file before the first
+send. Confirm the same file stays in the composer after the chat is created.
+Send it once, reload, and confirm the file and message remain.
+
 Manual: Start a conversation, send a recognizable request, and inspect its reply.
 Navigate away and reopen the same history. Use `/new` for a fresh session within
 the same standing conversation. Test an unavailable historical agent and an

ui/src/components/TaskChatThread.test.tsx

@@ -343,6 +343,46 @@ it.each([true, false])("defers hidden content until history is ready and keeps i
   expect(container.querySelector('.task-chat-history-pending')).toBeNull();
 });
 
+it("defers initial history for a saved conversation with its own draft key", () => {
+  render(<TaskChatThread comments={[]} onAdd={async () => {}} issueId="saved-chat"
+    conversationMode draftKey="agent-chat:company:saved-agent" initialHistoryPending />);
+  expect(container.querySelector('[data-testid="mock-editor"]')).toBeNull();
+  expect(container.querySelector('[data-testid="task-chat-composer-dock"]')?.hasAttribute("inert")).toBe(true);
+});
+
+it.each([true, false])("keeps an upload attached when a conversation draft becomes a saved task (mobile=%s)", async (mobile) => {
+  sidebarState.isMobile = mobile;
+  const onAdd = vi.fn().mockResolvedValue(undefined);
+  let resolveUpload!: (receipt: { id: string; contentPath: string; originalFilename: string }) => void;
+  const onAttachImage = vi.fn().mockReturnValue(new Promise(resolve => { resolveUpload = resolve; }));
+  const props = { comments: [], onAdd, onAttachImage, conversationMode: true, draftKey: "agent-chat:company:agent" };
+  render(<TaskChatThread {...props} issueId="" />);
+  const composer = container.querySelector('[data-testid="mock-editor"]');
+  const input = container.querySelector<HTMLInputElement>('input[type="file"]')!;
+  const file = new File(["notes"], "chat-notes.txt", { type: "text/plain" });
+  Object.defineProperty(input, "files", { configurable: true, value: [file] });
+  await act(async () => { input.dispatchEvent(new Event("change", { bubbles: true })); });
+  expect(onAttachImage).toHaveBeenCalledExactlyOnceWith(file);
+  expect(container.querySelector('[data-testid="task-chat-composer-attachments"]')?.textContent).toContain("chat-notes.txt");
+
+  render(<TaskChatThread {...props} issueId="persisted-chat" initialHistoryPending />);
+  expect(container.querySelector('[data-testid="mock-editor"]')).toBe(composer);
+  expect(container.querySelector('[data-testid="task-chat-composer-attachments"]')?.textContent).toContain("chat-notes.txt");
+  expect(onAdd).not.toHaveBeenCalled();
+  const id = "9af8228f-0be7-45ae-a104-6fbe0af6f1d3";
+  await act(async () => { resolveUpload({ id, contentPath: `/api/attachments/${id}/content`, originalFilename: file.name }); });
+  render(<TaskChatThread {...props} issueId="persisted-chat" initialHistoryPending={false} />);
+  await act(async () => { await new Promise(resolve => requestAnimationFrame(resolve)); });
+  const chip = container.querySelector('[data-testid="task-chat-composer-attachments"] [data-slot="attachment"]');
+  expect(chip?.getAttribute("data-state")).toBe("done");
+  const send = container.querySelector<HTMLButtonElement>('[data-testid="task-chat-composer-send"]')!;
+  expect(send.disabled).toBe(false);
+  await act(async () => { send.click(); });
+  expect(onAdd).toHaveBeenCalledTimes(1);
+  expect(onAdd.mock.calls[0]?.[0]).toBe(`[chat-notes.txt](/api/attachments/${id}/content)`);
+  expect(onAdd.mock.calls[0]?.[3]).toEqual([id]);
+});
+
 it("prepares comment-link history and its composer before reveal", async () => {
   const props = {
     issueId: "linked-issue",

ui/src/components/TaskChatThread.tsx

@@ -2924,12 +2924,13 @@ export function TaskChatThread(props: TaskChatThreadProps) {
           (logTranscriptByRun.get(run.id)?.length ?? 0) === 0
         : Boolean(logErrorsByRun?.has(run.id)),
     );
-  const [revealedIssue, setRevealedIssue] = useState<string | null | undefined>(
-    () => (historyPending ? undefined : issueId),
+  const historyKey = conversationMode && draftKey ? draftKey : issueId;
+  const [revealedHistoryKey, setRevealedHistoryKey] = useState<string | null | undefined>(
+    () => (historyPending ? undefined : historyKey),
   );
-  const historyRevealed = revealedIssue === issueId;
-  const [expiredHistoryWait, setExpiredHistoryWait] = useState<{ issueId: typeof issueId } | null>(null);
-  const historyWaitExpired = expiredHistoryWait !== null && expiredHistoryWait.issueId === issueId;
+  const historyRevealed = revealedHistoryKey === historyKey;
+  const [expiredHistoryWait, setExpiredHistoryWait] = useState<{ historyKey: typeof historyKey } | null>(null);
+  const historyWaitExpired = expiredHistoryWait !== null && expiredHistoryWait.historyKey === historyKey;
   const prepareInitialContent = Boolean(scrollNavigation.hash) || !historyPending || historyRevealed || historyWaitExpired;
   // Supporting requests can stall without rejecting. Bound the first reveal
   // independently of their pending states so saved conversation and the
@@ -2937,19 +2938,19 @@ export function TaskChatThread(props: TaskChatThreadProps) {
   useEffect(() => {
     if (historyRevealed) return;
     const timer = window.setTimeout(() => {
-      setExpiredHistoryWait({ issueId });
-      setRevealedIssue(issueId);
+      setExpiredHistoryWait({ historyKey });
+      setRevealedHistoryKey(historyKey);
     }, INITIAL_HISTORY_REVEAL_TIMEOUT_MS);
     return () => window.clearTimeout(timer);
-  }, [historyRevealed, issueId]);
+  }, [historyRevealed, historyKey]);
   // Mount and measure the real thread while concealed, then reveal in one
   // commit. A frame also lets ancestor navigation scroll restoration finish.
   // Readiness is latched per issue: refetches never hide existing conversation.
   useEffect(() => {
     if (historyRevealed || historyPending) return;
-    const frame = requestAnimationFrame(() => setRevealedIssue(issueId));
+    const frame = requestAnimationFrame(() => setRevealedHistoryKey(historyKey));
     return () => cancelAnimationFrame(frame);
-  }, [historyPending, historyRevealed, issueId]);
+  }, [historyPending, historyRevealed, historyKey]);
   useEffect(() => {
     if (!historyRevealed || !issueId) return;
     scheduleIssueDetailPaintMeasure(ISSUE_DETAIL_CONTENT_PAINT_MARK, ISSUE_DETAIL_CONTENT_MEASURE);