diff --git a/CHANGELOG.md b/CHANGELOG.md
index f85973ba9ae..00394e0802e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -42,6 +42,7 @@ Docs: https://docs.openclaw.ai
 ### Fixes
 
 - Release validation: install the cross-OS TypeScript harness through Windows-safe Node/npm shims so native Windows package checks reach the OpenClaw smoke suites instead of exiting before artifact capture. Thanks @vincentkoc.
+- Release validation: let Windows packaged-upgrade checks continue after the shipped 2026.5.2 updater hits its native-module swap cleanup fallback, verifying the fallback-installed candidate through package metadata and downstream smoke instead of crashing on the immediate update-status probe. Thanks @vincentkoc.
 - Agents/bootstrap: keep pending `BOOTSTRAP.md` and bootstrap truncation notices in system-prompt Project Context instead of copying setup text or raw warning diagnostics into WebChat user/runtime context. Fixes #76946.
 - Channels/WhatsApp: allow `@whiskeysockets/libsignal-node` in `onlyBuiltDependencies` so pnpm v9+ `blockExoticSubdeps` no longer rejects the baileys git-tarball subdep and silences all inbound agent replies. Fixes #76539. Thanks @ottodeng and @vincentkoc.
 - Gateway/install: keep `.env`-managed values in the macOS LaunchAgent env file while still tracking `OPENCLAW_SERVICE_MANAGED_ENV_KEYS`, so regenerated services do not boot without managed auth/provider keys. Fixes #75374.
diff --git a/scripts/openclaw-cross-os-release-checks.ts b/scripts/openclaw-cross-os-release-checks.ts
index cb11851a573..2449343116e 100644
--- a/scripts/openclaw-cross-os-release-checks.ts
+++ b/scripts/openclaw-cross-os-release-checks.ts
@@ -779,7 +779,9 @@ async function runUpgradeLane(params) {
       timeoutMs: updateTimeoutMs(),
       check: false,
     });
-    if (isRecoverableWindowsPackagedUpgradeSwapCleanupFailure(updateResult, process.platform)) {
+    const usedWindowsPackagedUpgradeFallback =
+      isRecoverableWindowsPackagedUpgradeSwapCleanupFailure(updateResult, process.platform);
+    if (usedWindowsPackagedUpgradeFallback) {
       logLanePhase(lane, "update-fallback-install");
       await installPackageSpec({
         lane,
@@ -793,14 +795,21 @@ async function runUpgradeLane(params) {
       });
     }
 
-    logLanePhase(lane, "update-status");
-    await runOpenClaw({
-      lane,
-      env: updateEnv,
-      args: ["update", "status", "--json"],
-      logPath: join(params.logsDir, "upgrade-update-status.log"),
-      timeoutMs: 2 * 60 * 1000,
-    });
+    if (
+      shouldRunPackagedUpgradeStatusProbe({
+        platform: process.platform,
+        usedWindowsPackagedUpgradeFallback,
+      })
+    ) {
+      logLanePhase(lane, "update-status");
+      await runOpenClaw({
+        lane,
+        env: updateEnv,
+        args: ["update", "status", "--json"],
+        logPath: join(params.logsDir, "upgrade-update-status.log"),
+        timeoutMs: 2 * 60 * 1000,
+      });
+    }
     logLanePhase(lane, "run-bundled-plugin-postinstall");
     await runBundledPluginPostinstall({
       lane,
@@ -1350,6 +1359,13 @@ export function isRecoverableWindowsPackagedUpgradeSwapCleanupFailure(
   );
 }
 
+export function shouldRunPackagedUpgradeStatusProbe({
+  platform = process.platform,
+  usedWindowsPackagedUpgradeFallback,
+} = {}) {
+  return !(platform === "win32" && usedWindowsPackagedUpgradeFallback);
+}
+
 export function resolveExplicitBaselineVersion(baselineSpec) {
   const trimmed = baselineSpec.trim();
   if (!trimmed || trimmed === "openclaw@latest") {
diff --git a/test/scripts/openclaw-cross-os-release-checks.test.ts b/test/scripts/openclaw-cross-os-release-checks.test.ts
index 575cdbac9af..5ea01e8aca8 100644
--- a/test/scripts/openclaw-cross-os-release-checks.test.ts
+++ b/test/scripts/openclaw-cross-os-release-checks.test.ts
@@ -53,6 +53,7 @@ import {
   resolveRunnerMatrix,
   resolveStaticFileContentType,
   shouldExerciseManagedGatewayLifecycleAfterInstall,
+  shouldRunPackagedUpgradeStatusProbe,
   shouldRunWindowsInstalledBrowserOverrideImportSmoke,
   shouldSkipInstallerDaemonHealthCheck,
   shouldStopManagedGatewayBeforeManualFallback,
@@ -716,6 +717,27 @@ describe("scripts/openclaw-cross-os-release-checks", () => {
     ).toBe(true);
   });
 
+  it("skips the packaged upgrade status probe after the Windows fallback install", () => {
+    expect(
+      shouldRunPackagedUpgradeStatusProbe({
+        platform: "win32",
+        usedWindowsPackagedUpgradeFallback: true,
+      }),
+    ).toBe(false);
+    expect(
+      shouldRunPackagedUpgradeStatusProbe({
+        platform: "win32",
+        usedWindowsPackagedUpgradeFallback: false,
+      }),
+    ).toBe(true);
+    expect(
+      shouldRunPackagedUpgradeStatusProbe({
+        platform: "linux",
+        usedWindowsPackagedUpgradeFallback: true,
+      }),
+    ).toBe(true);
+  });
+
   it("does not recover unrelated packaged update failures", () => {
     expect(
       isRecoverableWindowsPackagedUpgradeSwapCleanupFailure(