diff --git a/PRODUCT.md b/PRODUCT.md
index c3079f032..389e1bfa3 100644
--- a/PRODUCT.md
+++ b/PRODUCT.md
@@ -44,7 +44,7 @@ No public inbound ports are required for normal usage.
 ### Session management
 
 - Fetch last N sessions (name + date)
-- Select an existing session, show the last user input as a quote and the last assistant reply in full, then follow its live updates
+- Select an existing session, show the last user input as a quote and the last assistant reply in full (plus the newest input still waiting for its reply), then follow its live updates
 - Browse up to `SESSIONS_LIST_LIMIT` recent root sessions across projects and git worktrees with running, idle, question and permission status (a question or permission request a subagent is waiting on counts for its root session); select one to switch project and follow it, including after detach
 - Switching to an existing session adopts the agent, model, and variant it last ran with
 - Create a new session
diff --git a/src/app/services/session-pick-reply.ts b/src/app/services/session-pick-reply.ts
index e4103f1eb..12ad23c1d 100644
--- a/src/app/services/session-pick-reply.ts
+++ b/src/app/services/session-pick-reply.ts
@@ -110,6 +110,23 @@ export function findMessageById(
   return messages.find((message) => message.info.id === messageId) ?? null;
 }
 
+/**
+ * The newest user input the transcript does not already cover: a message created after the
+ * shown reply started, still waiting for its own reply. Compared by time rather than by the
+ * reply's parent, because the V2 adapter carries no parent link.
+ */
+export function findPendingUserPrompt(
+  messages: SessionPickMessage[],
+  shownReplyCreated: number,
+): SessionPickMessage | null {
+  const latest = findLatestUserPrompt(messages);
+  if (!latest) {
+    return null;
+  }
+
+  return (latest.info.time?.created ?? 0) > shownReplyCreated ? latest : null;
+}
+
 export function buildSessionPickQuote(message: SessionPickMessage): QuotedNotification | null {
   const text = extractText(message.parts);
   const body = text ?? fileLines(message.parts).join("\n");
diff --git a/src/bot/callbacks/session-callback-handler.ts b/src/bot/callbacks/session-callback-handler.ts
index d4bdfe71d..8d90b5758 100644
--- a/src/bot/callbacks/session-callback-handler.ts
+++ b/src/bot/callbacks/session-callback-handler.ts
@@ -28,8 +28,10 @@ import {
   findEligibleReply,
   findLatestUserPrompt,
   findMessageById,
+  findPendingUserPrompt,
   type SessionPickMessage,
 } from "../../app/services/session-pick-reply.js";
+import type { QuotedNotification } from "../../app/services/quoted-notification.js";
 import {
   buildSessionSelectionMenuView,
   parseBackgroundSessionCallback,
@@ -488,6 +490,25 @@ async function loadParentMessage(
   }
 }
 
+async function sendPickQuote(
+  api: Context["api"],
+  chatId: number,
+  quote: QuotedNotification,
+): Promise<void> {
+  await waitForSessionPickSend();
+  try {
+    await sendBotText({
+      api,
+      chatId,
+      text: quote.text,
+      rawFallbackText: quote.rawFallbackText,
+      format: "markdown_v2",
+    });
+  } catch (err) {
+    logger.error("[Sessions] Failed to send the session pick quote:", err);
+  }
+}
+
 async function sendSessionPickTranscript(
   api: Context["api"],
   chatId: number,
@@ -510,18 +531,7 @@ async function sendSessionPickTranscript(
 
   const quote = quoteSource ? buildSessionPickQuote(quoteSource) : null;
   if (quote) {
-    await waitForSessionPickSend();
-    try {
-      await sendBotText({
-        api,
-        chatId,
-        text: quote.text,
-        rawFallbackText: quote.rawFallbackText,
-        format: "markdown_v2",
-      });
-    } catch (err) {
-      logger.error("[Sessions] Failed to send the last user input quote:", err);
-    }
+    await sendPickQuote(api, chatId, quote);
   } else if (!reply) {
     await waitForSessionPickSend();
     try {
@@ -540,6 +550,14 @@ async function sendSessionPickTranscript(
     await waitForSessionPickSend();
     await sendRenderedBotPart({ api, chatId, part, options: AGENT_TEXT_LINK_PREVIEW_OPTIONS });
   }
+
+  // A message sent after the shown reply started is still waiting for its own reply: show it
+  // too, so the picked session does not look like the message never went through.
+  const pendingPrompt = messages ? findPendingUserPrompt(messages, reply.created) : null;
+  const pendingQuote = pendingPrompt ? buildSessionPickQuote(pendingPrompt) : null;
+  if (pendingQuote) {
+    await sendPickQuote(api, chatId, pendingQuote);
+  }
 }
 
 async function loadLatestAssistantResponse(
diff --git a/tests/app/services/session-pick-reply.test.ts b/tests/app/services/session-pick-reply.test.ts
index 79dadf671..6aa11fad1 100644
--- a/tests/app/services/session-pick-reply.test.ts
+++ b/tests/app/services/session-pick-reply.test.ts
@@ -3,6 +3,7 @@ import {
   buildSessionPickQuote,
   findEligibleReply,
   findLatestUserPrompt,
+  findPendingUserPrompt,
   type SessionPickMessage,
 } from "../../../src/app/services/session-pick-reply.js";
 
@@ -63,6 +64,53 @@ describe("session pick reply", () => {
     expect(findLatestUserPrompt(messages)?.info.id).toBe("user-1");
   });
 
+  it("returns the newest prompt when it was created after the shown reply", () => {
+    const messages = [
+      message("user", "answered prompt", 1, { id: "user-old" }),
+      message("assistant", "reply", 2, {
+        id: "assistant-1",
+        parentID: "user-old",
+        time: { created: 2, completed: 3 },
+      }),
+      message("user", "waiting prompt", 4, { id: "user-new" }),
+    ];
+
+    expect(findPendingUserPrompt(messages, 2)?.info.id).toBe("user-new");
+  });
+
+  it("returns the newest prompt when several were created after the shown reply", () => {
+    const messages = [
+      message("user", "answered prompt", 1, { id: "user-old" }),
+      message("assistant", "reply", 2, {
+        id: "assistant-1",
+        parentID: "user-old",
+        time: { created: 2, completed: 3 },
+      }),
+      message("user", "first waiting prompt", 4, { id: "user-mid" }),
+      message("user", "second waiting prompt", 5, { id: "user-new" }),
+    ];
+
+    expect(findPendingUserPrompt(messages, 2)?.info.id).toBe("user-new");
+  });
+
+  it("returns nothing when the newest prompt predates the shown reply", () => {
+    const messages = [
+      message("user", "the prompt", 1, { id: "user-1" }),
+      message("assistant", "reply", 2, {
+        id: "assistant-1",
+        parentID: "user-1",
+        time: { created: 2, completed: 3 },
+      }),
+    ];
+
+    expect(findPendingUserPrompt(messages, 2)).toBeNull();
+    expect(findPendingUserPrompt(messages, 3)).toBeNull();
+  });
+
+  it("returns nothing when the session has no user prompt", () => {
+    expect(findPendingUserPrompt([message("assistant", "reply", 1)], 1)).toBeNull();
+  });
+
   it("drops an in-flight reply while the session is busy", () => {
     const selected = findEligibleReply(
       [
diff --git a/tests/bot/commands/sessions.test.ts b/tests/bot/commands/sessions.test.ts
index 10ddd6b05..8531fa353 100644
--- a/tests/bot/commands/sessions.test.ts
+++ b/tests/bot/commands/sessions.test.ts
@@ -516,7 +516,7 @@ describe("bot/commands/sessions", () => {
     );
   });
 
-  it("pages past a newer prompt and shows the finished reply it answers", async () => {
+  it("pages past a newer prompt and shows the finished reply it answers plus the waiting prompt", async () => {
     mocked.sessionGetMock.mockResolvedValueOnce({
       data: createSession(0),
       error: null,
@@ -529,7 +529,7 @@ describe("bot/commands/sessions", () => {
       },
       parts:
         index === 19
-          ? [{ type: "text", text: "unanswered prompt" }]
+          ? [{ type: "text", text: "newer prompt" }]
           : [{ type: "tool" }],
     }));
     mocked.sessionMessagesMock.mockReset();
@@ -543,7 +543,7 @@ describe("bot/commands/sessions", () => {
               role: "user",
               time: { created: 100 },
             },
-            parts: [{ type: "text", text: "answered prompt" }],
+            parts: [{ type: "text", text: "older prompt" }],
           },
           {
             info: {
@@ -579,15 +579,17 @@ describe("bot/commands/sessions", () => {
     const sent = (ctx.api.sendMessage as ReturnType<typeof vi.fn>).mock.calls.map(
       (call) => String(call[1]),
     );
-    expect(sent.some((text) => text.includes("answered prompt"))).toBe(true);
+    expect(sent.some((text) => text.includes("older prompt"))).toBe(true);
     expect(sent.some((text) => text.includes("finished reply"))).toBe(true);
-    expect(sent.some((text) => text.includes("unanswered prompt"))).toBe(false);
     expect(sent.some((text) => text.includes("Recent messages:"))).toBe(false);
+    const replyIndex = sent.findIndex((text) => text.includes("finished reply"));
+    const waitingIndex = sent.findIndex((text) => text.includes("newer prompt"));
+    expect(waitingIndex).toBeGreaterThan(replyIndex);
     expect(safeBackgroundTaskMock).not.toHaveBeenCalled();
 
     const sendCalls = (ctx.api.sendMessage as ReturnType<typeof vi.fn>).mock.calls;
     const replyCall = sendCalls.find((call) => String(call[1]).includes("finished reply"));
-    const quoteCall = sendCalls.find((call) => String(call[1]).includes("answered prompt"));
+    const quoteCall = sendCalls.find((call) => String(call[1]).includes("older prompt"));
     expect(replyCall?.[2]).toMatchObject({ link_preview_options: { is_disabled: false } });
     expect(quoteCall?.[2]).not.toHaveProperty("link_preview_options");
   });