fix(code): reliable cloud message-queue dispatch + optimistic prompt UX

apps/code/src/renderer/features/sessions/components/ConversationView.tsx

@@ -22,6 +22,7 @@ import {
 } from "./buildConversationItems";
 import { GitActionMessage } from "./GitActionMessage";
 import { GitActionResult } from "./GitActionResult";
+import { mergeConversationItems } from "./mergeConversationItems";
 import { SessionFooter } from "./SessionFooter";
 import { QueuedMessageView } from "./session-update/QueuedMessageView";
 import {
@@ -117,13 +118,18 @@ export function ConversationView({
     [queuedMessages],
   );
 
-  const items = useMemo<ConversationItem[]>(() => {
-    const result: ConversationItem[] = [
-      ...conversationItems,
-      ...optimisticItems,
-    ];
-    return queuedItems.length > 0 ? [...result, ...queuedItems] : result;
-  }, [conversationItems, optimisticItems, queuedItems]);
+  const isCloud = session?.isCloud ?? false;
+
+  const items = useMemo<ConversationItem[]>(
+    () =>
+      mergeConversationItems({
+        conversationItems,
+        optimisticItems,
+        queuedItems,
+        isCloud,
+      }),
+    [conversationItems, optimisticItems, queuedItems, isCloud],
+  );
 
   // Keep MCP App tool call items mounted so their iframes and bridges
   // survive scrolling out of the virtualized viewport.

apps/code/src/renderer/features/sessions/components/mergeConversationItems.test.ts

@@ -0,0 +1,102 @@
+import type { QueuedMessage } from "@features/sessions/stores/sessionStore";
+import { describe, expect, it } from "vitest";
+import type { ConversationItem } from "./buildConversationItems";
+import { mergeConversationItems } from "./mergeConversationItems";
+
+function userMessage(
+  id: string,
+  content: string,
+): Extract<ConversationItem, { type: "user_message" }> {
+  return { type: "user_message", id, content, timestamp: 0 };
+}
+
+function queuedItem(
+  id: string,
+  content: string,
+): Extract<ConversationItem, { type: "queued" }> {
+  const message: QueuedMessage = {
+    id,
+    content,
+    rawPrompt: [{ type: "text", text: content }],
+    queuedAt: 0,
+  };
+  return { type: "queued", id, message };
+}
+
+describe("mergeConversationItems", () => {
+  it("local: appends optimistic at the chronological end", () => {
+    const result = mergeConversationItems({
+      conversationItems: [userMessage("a", "first")],
+      optimisticItems: [userMessage("opt", "draft")],
+      queuedItems: [],
+      isCloud: false,
+    });
+    expect(result.map((i) => i.id)).toEqual(["a", "opt"]);
+  });
+
+  it("local: queued items always come last", () => {
+    const result = mergeConversationItems({
+      conversationItems: [userMessage("a", "first")],
+      optimisticItems: [userMessage("opt", "draft")],
+      queuedItems: [queuedItem("q1", "later")],
+      isCloud: false,
+    });
+    expect(result.map((i) => i.id)).toEqual(["a", "opt", "q1"]);
+  });
+
+  it("local: does NOT dedupe — duplicate echoes are intentionally retained", () => {
+    const result = mergeConversationItems({
+      conversationItems: [userMessage("echo", "hello")],
+      optimisticItems: [userMessage("opt", "hello")],
+      queuedItems: [],
+      isCloud: false,
+    });
+    expect(result.map((i) => i.id)).toEqual(["echo", "opt"]);
+  });
+
+  it("cloud: pins optimistic at the top", () => {
+    const result = mergeConversationItems({
+      conversationItems: [userMessage("setup", "setup info")],
+      optimisticItems: [userMessage("opt", "draft")],
+      queuedItems: [],
+      isCloud: true,
+    });
+    expect(result.map((i) => i.id)).toEqual(["opt", "setup"]);
+  });
+
+  it("cloud: filters echoed user_message that matches optimistic content", () => {
+    const result = mergeConversationItems({
+      conversationItems: [
+        userMessage("echo", "hello"),
+        userMessage("other", "different"),
+      ],
+      optimisticItems: [userMessage("opt", "hello")],
+      queuedItems: [],
+      isCloud: true,
+    });
+    expect(result.map((i) => i.id)).toEqual(["opt", "other"]);
+  });
+
+  it("cloud: dedupe is no-op when there are no optimistic items", () => {
+    const result = mergeConversationItems({
+      conversationItems: [
+        userMessage("a", "first"),
+        userMessage("b", "second"),
+      ],
+      optimisticItems: [],
+      queuedItems: [],
+      isCloud: true,
+    });
+    expect(result.map((i) => i.id)).toEqual(["a", "b"]);
+  });
+
+  it("cloud: queued items always come last", () => {
+    const result = mergeConversationItems({
+      conversationItems: [userMessage("setup", "setup")],
+      optimisticItems: [userMessage("opt", "draft")],
+      queuedItems: [queuedItem("q1", "later")],
+      isCloud: true,
+    });
+    expect(result.map((i) => i.id)).toEqual(["opt", "setup", "q1"]);
+  });
+});

apps/code/src/renderer/features/sessions/components/mergeConversationItems.ts

@@ -0,0 +1,53 @@
+import type { ConversationItem } from "./buildConversationItems";
+
+type QueuedItem = Extract<ConversationItem, { type: "queued" }>;
+
+interface MergeConversationItemsArgs {
+  conversationItems: ConversationItem[];
+  optimisticItems: ConversationItem[];
+  queuedItems: QueuedItem[];
+  isCloud: boolean;
+}
+
+// Cloud's initial optimistic is pinned to the top so the user's prompt stays
+// visible above setup progress. When the agent echoes it back via
+// `session/prompt`, the duplicate `user_message` is filtered out by content
+// match so the bubble doesn't disappear-then-reappear when the echo lands.
+//
+// Local sessions keep optimistic at the chronological end — they rely on
+// `replaceOptimisticWithEvent` to swap optimistic↔real in place.
+export function mergeConversationItems({
+  conversationItems,
+  optimisticItems,
+  queuedItems,
+  isCloud,
+}: MergeConversationItemsArgs): ConversationItem[] {
+  if (!isCloud) {
+    const result: ConversationItem[] = [
+      ...conversationItems,
+      ...optimisticItems,
+    ];
+    return queuedItems.length > 0 ? [...result, ...queuedItems] : result;
+  }
+
+  const optimisticUserContents = new Set(
+    optimisticItems
+      .filter(
+        (item): item is Extract<typeof item, { type: "user_message" }> =>
+          item.type === "user_message",
+      )
+      .map((item) => item.content),
+  );
+  const dedupedConversation =
+    optimisticUserContents.size === 0
+      ? conversationItems
+      : conversationItems.filter((item) => {
+          if (item.type !== "user_message") return true;
+          return !optimisticUserContents.has(item.content);
+        });
+  const result: ConversationItem[] = [
+    ...optimisticItems,
+    ...dedupedConversation,
+  ];
+  return queuedItems.length > 0 ? [...result, ...queuedItems] : result;
+}

apps/code/src/renderer/features/sessions/hooks/useSessionConnection.ts

@@ -91,6 +91,7 @@ export function useSessionConnection({
       initialMode,
       adapter,
       initialModel,
+      task.description ?? undefined,
     );
     return cleanup;
   }, [
@@ -106,6 +107,7 @@ export function useSessionConnection({
     task.latest_run?.model,
     task.latest_run?.runtime_adapter,
     task.latest_run?.state?.initial_permission_mode,
+    task.description,
   ]);
 
   useEffect(() => {