diff --git a/scripts/openclaw-cross-os-release-checks.ts b/scripts/openclaw-cross-os-release-checks.ts
index 2449343116e..4b6fe265fee 100644
--- a/scripts/openclaw-cross-os-release-checks.ts
+++ b/scripts/openclaw-cross-os-release-checks.ts
@@ -119,6 +119,9 @@ export const CROSS_OS_GATEWAY_STATUS_COMMAND_TIMEOUT_MS =
 export const CROSS_OS_GATEWAY_READY_TIMEOUT_MS = 3 * 60_000;
 export const CROSS_OS_WINDOWS_GATEWAY_READY_TIMEOUT_MS = 5 * 60_000;
 export const CROSS_OS_RELEASE_SMOKE_TOOLS_PROFILE = "minimal";
+export const CROSS_OS_WINDOWS_PACKAGED_UPGRADE_STEP_TIMEOUT_SECONDS = 25 * 60;
+export const CROSS_OS_WINDOWS_PACKAGED_UPGRADE_WRAPPER_TIMEOUT_MS =
+  (CROSS_OS_WINDOWS_PACKAGED_UPGRADE_STEP_TIMEOUT_SECONDS + 5 * 60) * 1000;
 
 if (isMainModule()) {
   try {
@@ -2413,11 +2416,15 @@ function installTimeoutMs() {
 }
 
 function updateTimeoutMs() {
-  return process.platform === "win32" ? 30 * 60 * 1000 : 20 * 60 * 1000;
+  return process.platform === "win32"
+    ? CROSS_OS_WINDOWS_PACKAGED_UPGRADE_WRAPPER_TIMEOUT_MS
+    : 20 * 60 * 1000;
 }
 
 function updateStepTimeoutSeconds() {
-  return process.platform === "win32" ? 1800 : 1200;
+  return process.platform === "win32"
+    ? CROSS_OS_WINDOWS_PACKAGED_UPGRADE_STEP_TIMEOUT_SECONDS
+    : 1200;
 }
 
 async function runBundledPluginPostinstall(params) {
diff --git a/test/scripts/openclaw-cross-os-release-checks.test.ts b/test/scripts/openclaw-cross-os-release-checks.test.ts
index 5ea01e8aca8..ba536f51e0d 100644
--- a/test/scripts/openclaw-cross-os-release-checks.test.ts
+++ b/test/scripts/openclaw-cross-os-release-checks.test.ts
@@ -30,6 +30,8 @@ import {
   CROSS_OS_GATEWAY_STATUS_RPC_TIMEOUT_MS,
   CROSS_OS_RELEASE_SMOKE_TOOLS_PROFILE,
   CROSS_OS_WINDOWS_GATEWAY_READY_TIMEOUT_MS,
+  CROSS_OS_WINDOWS_PACKAGED_UPGRADE_STEP_TIMEOUT_SECONDS,
+  CROSS_OS_WINDOWS_PACKAGED_UPGRADE_WRAPPER_TIMEOUT_MS,
   CROSS_OS_DASHBOARD_FETCH_TIMEOUT_MS,
   CROSS_OS_DASHBOARD_SMOKE_TIMEOUT_MS,
   CROSS_OS_AGENT_TURN_TIMEOUT_SECONDS,
@@ -82,6 +84,17 @@ describe("scripts/openclaw-cross-os-release-checks", () => {
     expect(CROSS_OS_WINDOWS_GATEWAY_READY_TIMEOUT_MS).toBeGreaterThanOrEqual(300_000);
   });
 
+  it("gives the Windows packaged updater wrapper enough headroom for OpenClaw timeout output", () => {
+    expect(CROSS_OS_WINDOWS_PACKAGED_UPGRADE_STEP_TIMEOUT_SECONDS).toBeGreaterThanOrEqual(20 * 60);
+    expect(CROSS_OS_WINDOWS_PACKAGED_UPGRADE_WRAPPER_TIMEOUT_MS).toBeGreaterThan(
+      CROSS_OS_WINDOWS_PACKAGED_UPGRADE_STEP_TIMEOUT_SECONDS * 1000,
+    );
+    expect(
+      CROSS_OS_WINDOWS_PACKAGED_UPGRADE_WRAPPER_TIMEOUT_MS -
+        CROSS_OS_WINDOWS_PACKAGED_UPGRADE_STEP_TIMEOUT_SECONDS * 1000,
+    ).toBeGreaterThanOrEqual(5 * 60 * 1000);
+  });
+
   it("accepts OK agent output from the captured log when stdout is empty", () => {
     const dir = mkdtempSync(join(tmpdir(), "openclaw-cross-os-agent-output-"));
     try {