diff --git a/src/config/sessions/transcript.test.ts b/src/config/sessions/transcript.test.ts
new file mode 100644
index 00000000000..0a87b52bbc4
--- /dev/null
+++ b/src/config/sessions/transcript.test.ts
@@ -0,0 +1,112 @@
+import fs from "node:fs";
+import os from "node:os";
+import path from "node:path";
+import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
+import type { SessionEntry } from "./types.js";
+
+const state = vi.hoisted(() => ({
+  sessionFile: "",
+  store: {} as Record<string, SessionEntry>,
+  appendMessage: vi.fn(() => "message-1"),
+}));
+
+vi.mock("../io.js", () => ({
+  loadConfig: () => ({
+    agents: {
+      list: [{ id: "sunke", default: true }],
+    },
+  }),
+}));
+
+vi.mock("../../agents/agent-scope.js", () => ({
+  resolveDefaultAgentId: () => "sunke",
+  resolveAgentWorkspaceDir: (_cfg: unknown, agentId: string) =>
+    `/Users/admin/.openclaw/workspace-${agentId}`,
+}));
+
+vi.mock("../../sessions/transcript-events.js", () => ({
+  emitSessionTranscriptUpdate: vi.fn(),
+}));
+
+vi.mock("./delivery-info.js", () => ({
+  parseSessionThreadInfo: () => ({ baseSessionKey: undefined, threadId: undefined }),
+}));
+
+vi.mock("./paths.js", () => ({
+  resolveDefaultSessionStorePath: () => "/tmp/session-store.json",
+  resolveSessionFilePath: () => state.sessionFile,
+  resolveSessionFilePathOptions: () => ({
+    agentId: "sunke",
+    sessionsDir: path.dirname(state.sessionFile),
+  }),
+  resolveSessionTranscriptPath: () => state.sessionFile,
+}));
+
+vi.mock("./session-file.js", () => ({
+  resolveAndPersistSessionFile: async () => ({
+    sessionFile: state.sessionFile,
+    sessionEntry: state.store["agent:main:test:user-1"],
+  }),
+}));
+
+vi.mock("./store.js", () => ({
+  loadSessionStore: () => state.store,
+  normalizeStoreSessionKey: (value: string) => value,
+}));
+
+vi.mock("@mariozechner/pi-coding-agent", () => ({
+  CURRENT_SESSION_VERSION: 2,
+  SessionManager: {
+    open: () => ({
+      appendMessage: state.appendMessage,
+    }),
+  },
+}));
+
+let appendAssistantMessageToSessionTranscript: typeof import("./transcript.js").appendAssistantMessageToSessionTranscript;
+const originalCwd = process.cwd();
+
+beforeEach(async () => {
+  vi.resetModules();
+  state.appendMessage = vi.fn(() => "message-1");
+  state.store = {
+    "agent:main:test:user-1": {
+      sessionId: "session-1",
+      updatedAt: Date.now(),
+    } as SessionEntry,
+  };
+
+  const tmpRoot = fs.mkdtempSync(path.join(os.tmpdir(), "openclaw-transcript-"));
+  const wrongWorkspace = path.join(tmpRoot, "wrong-workspace");
+  fs.mkdirSync(wrongWorkspace, { recursive: true });
+  process.chdir(wrongWorkspace);
+
+  state.sessionFile = path.join(tmpRoot, "sessions", "session-1.jsonl");
+  ({ appendAssistantMessageToSessionTranscript } = await import("./transcript.js"));
+});
+
+afterEach(() => {
+  process.chdir(originalCwd);
+});
+
+describe("appendAssistantMessageToSessionTranscript", () => {
+  it("writes the session header cwd from the target agent workspace instead of process.cwd()", async () => {
+    const result = await appendAssistantMessageToSessionTranscript({
+      agentId: "sunke",
+      sessionKey: "agent:main:test:user-1",
+      text: "hello",
+    });
+
+    expect(result).toEqual({
+      ok: true,
+      sessionFile: state.sessionFile,
+      messageId: "message-1",
+    });
+
+    const [headerLine] = fs.readFileSync(state.sessionFile, "utf-8").split(/\r?\n/);
+    const header = JSON.parse(headerLine) as { cwd?: string };
+
+    expect(header.cwd).toBe("/Users/admin/.openclaw/workspace-sunke");
+    expect(header.cwd).not.toBe(process.cwd());
+  });
+});
diff --git a/src/config/sessions/transcript.ts b/src/config/sessions/transcript.ts
index aba99d02945..3ee4d39fcb6 100644
--- a/src/config/sessions/transcript.ts
+++ b/src/config/sessions/transcript.ts
@@ -1,7 +1,9 @@
 import fs from "node:fs";
 import path from "node:path";
 import { CURRENT_SESSION_VERSION, SessionManager } from "@mariozechner/pi-coding-agent";
+import { resolveDefaultAgentId, resolveAgentWorkspaceDir } from "../../agents/agent-scope.js";
 import { emitSessionTranscriptUpdate } from "../../sessions/transcript-events.js";
+import { loadConfig } from "../io.js";
 import { parseSessionThreadInfo } from "./delivery-info.js";
 import {
   resolveDefaultSessionStorePath,
@@ -67,6 +69,7 @@ export function resolveMirroredTranscriptText(params: {
 async function ensureSessionHeader(params: {
   sessionFile: string;
   sessionId: string;
+  cwd: string;
 }): Promise<void> {
   if (fs.existsSync(params.sessionFile)) {
     return;
@@ -77,7 +80,7 @@ async function ensureSessionHeader(params: {
     version: CURRENT_SESSION_VERSION,
     id: params.sessionId,
     timestamp: new Date().toISOString(),
-    cwd: process.cwd(),
+    cwd: params.cwd,
   };
   await fs.promises.writeFile(params.sessionFile, `${JSON.stringify(header)}\n`, {
     encoding: "utf-8",
@@ -160,6 +163,13 @@ export async function appendAssistantMessageToSessionTranscript(params: {
     return { ok: false, reason: `unknown sessionKey: ${sessionKey}` };
   }
 
+  const cfg = loadConfig();
+  const agentId =
+    typeof params.agentId === "string" && params.agentId.trim()
+      ? params.agentId.trim()
+      : resolveDefaultAgentId(cfg);
+  const sessionCwd = resolveAgentWorkspaceDir(cfg, agentId);
+
   let sessionFile: string;
   try {
     const resolvedSessionFile = await resolveAndPersistSessionFile({
@@ -179,7 +189,11 @@ export async function appendAssistantMessageToSessionTranscript(params: {
     };
   }
 
-  await ensureSessionHeader({ sessionFile, sessionId: entry.sessionId });
+  await ensureSessionHeader({
+    sessionFile,
+    sessionId: entry.sessionId,
+    cwd: sessionCwd,
+  });
 
   const existingMessageId = params.idempotencyKey
     ? await transcriptHasIdempotencyKey(sessionFile, params.idempotencyKey)