diff --git a/frontend/app/app/assistant.tsx b/frontend/app/app/assistant.tsx
index 5ae90cf..acf177d 100644
--- a/frontend/app/app/assistant.tsx
+++ b/frontend/app/app/assistant.tsx
@@ -20,6 +20,7 @@ import {
 	SidebarTrigger,
 } from "@/components/ui/sidebar";
 import {
+	consumePendingWorkspaceSessionId,
 	readActiveSessionId,
 	writeActiveSessionId,
 } from "@/lib/claw-active-session";
@@ -37,10 +38,21 @@ export const Assistant = () => {
 					const messages = options.messages as UIMessage[];
 					const selectedSessionId = readActiveSessionId();
 					const lastSessionId = getLastSessionId(messages);
+					const pendingWorkspaceSessionId =
+						messages.length <= 1 ? consumePendingWorkspaceSessionId() : null;
+					const usablePendingWorkspaceSessionId =
+						pendingWorkspaceSessionId &&
+						(!selectedSessionId ||
+							selectedSessionId === pendingWorkspaceSessionId)
+							? pendingWorkspaceSessionId
+							: null;
 					const selectedResumeSessionId =
 						messages.length > 1 ? selectedSessionId : null;
 					const outgoingSessionId =
-						lastSessionId ?? selectedResumeSessionId ?? options.id;
+						lastSessionId ??
+						selectedResumeSessionId ??
+						usablePendingWorkspaceSessionId ??
+						options.id;
 					const lastUserMessage = [...messages]
 						.reverse()
 						.find((message) => message.role === "user");
@@ -49,7 +61,7 @@ export const Assistant = () => {
 					return {
 						body: {
 							...body,
-							id: options.id,
+							id: outgoingSessionId,
 							messages: lastUserMessage ? [lastUserMessage] : [],
 							resumeSessionId:
 								lastSessionId ?? selectedResumeSessionId ?? undefined,
diff --git a/frontend/app/components/assistant-ui/thread.tsx b/frontend/app/components/assistant-ui/thread.tsx
index 9326d74..10ca8a0 100644
--- a/frontend/app/components/assistant-ui/thread.tsx
+++ b/frontend/app/components/assistant-ui/thread.tsx
@@ -83,6 +83,7 @@ import {
 	clearActiveSessionId,
 	readActiveSessionId,
 	writeActiveSessionId,
+	writePendingWorkspaceSessionId,
 } from "@/lib/claw-active-session";
 import { useClawSessionReplay } from "@/lib/claw-session-replay";
 import { cn } from "@/lib/utils";
@@ -437,6 +438,7 @@ function WorkspaceSwitchDialog({
 		setSubmitting(true);
 		const progressTimer = startWorkspaceProgress(setProgress);
 		try {
+			const needsFirstMessageSession = !normalizeSessionId(sessionId);
 			const response = await fetch("/api/claw/jupyter", {
 				method: "POST",
 				headers: { "content-type": "application/json" },
@@ -455,6 +457,9 @@ function WorkspaceSwitchDialog({
 				return;
 			}
 			writeActiveSessionId(sessionIdForRequest);
+			if (needsFirstMessageSession) {
+				writePendingWorkspaceSessionId(sessionIdForRequest);
+			}
 			setStatus(payload as JupyterWorkspaceStatus);
 			setProgress({ percent: 100, label: "切换完成" });
 			setMessage("工作区切换成功，后续工具会在远端 Jupyter 工作区执行。");
diff --git a/frontend/app/lib/claw-active-session.ts b/frontend/app/lib/claw-active-session.ts
index 5227b98..252f9e1 100644
--- a/frontend/app/lib/claw-active-session.ts
+++ b/frontend/app/lib/claw-active-session.ts
@@ -1,6 +1,7 @@
 "use client";
 
 const ACTIVE_SESSION_ID_KEY = "claw.activeSessionId";
+const PENDING_WORKSPACE_SESSION_ID_KEY = "claw.pendingWorkspaceSessionId";
 export const ACTIVE_SESSION_CHANGED_EVENT = "claw-active-session-changed";
 
 export function readActiveSessionId() {
@@ -20,6 +21,10 @@ export function writeActiveSessionId(sessionId: string | null | undefined) {
 	}
 	window.sessionStorage.setItem(ACTIVE_SESSION_ID_KEY, normalized);
 	window.localStorage.setItem(ACTIVE_SESSION_ID_KEY, normalized);
+	const pendingSessionId = readPendingWorkspaceSessionId();
+	if (pendingSessionId && pendingSessionId !== normalized) {
+		clearPendingWorkspaceSessionId();
+	}
 	window.dispatchEvent(
 		new CustomEvent(ACTIVE_SESSION_CHANGED_EVENT, {
 			detail: { sessionId: normalized },
@@ -31,6 +36,7 @@ export function clearActiveSessionId() {
 	if (typeof window === "undefined") return;
 	window.sessionStorage.removeItem(ACTIVE_SESSION_ID_KEY);
 	window.localStorage.removeItem(ACTIVE_SESSION_ID_KEY);
+	clearPendingWorkspaceSessionId();
 	window.dispatchEvent(
 		new CustomEvent(ACTIVE_SESSION_CHANGED_EVENT, {
 			detail: { sessionId: null },
@@ -38,6 +44,43 @@ export function clearActiveSessionId() {
 	);
 }
 
+export function writePendingWorkspaceSessionId(
+	sessionId: string | null | undefined,
+) {
+	if (typeof window === "undefined") return;
+	const normalized = normalizeSessionId(sessionId);
+	if (!normalized) {
+		clearPendingWorkspaceSessionId();
+		return;
+	}
+	window.sessionStorage.setItem(PENDING_WORKSPACE_SESSION_ID_KEY, normalized);
+	window.localStorage.setItem(PENDING_WORKSPACE_SESSION_ID_KEY, normalized);
+}
+
+export function consumePendingWorkspaceSessionId() {
+	const sessionId = readPendingWorkspaceSessionId();
+	clearPendingWorkspaceSessionId();
+	return sessionId;
+}
+
+function readPendingWorkspaceSessionId() {
+	if (typeof window === "undefined") return null;
+	return (
+		normalizeSessionId(
+			window.sessionStorage.getItem(PENDING_WORKSPACE_SESSION_ID_KEY),
+		) ??
+		normalizeSessionId(
+			window.localStorage.getItem(PENDING_WORKSPACE_SESSION_ID_KEY),
+		)
+	);
+}
+
+function clearPendingWorkspaceSessionId() {
+	if (typeof window === "undefined") return;
+	window.sessionStorage.removeItem(PENDING_WORKSPACE_SESSION_ID_KEY);
+	window.localStorage.removeItem(PENDING_WORKSPACE_SESSION_ID_KEY);
+}
+
 function normalizeSessionId(value: unknown) {
 	if (typeof value !== "string") return null;
 	const trimmed = value.trim();