diff --git a/src/cli/update-cli/restart-helper.test.ts b/src/cli/update-cli/restart-helper.test.ts
index 1e15556d89e..c8b59d69afa 100644
--- a/src/cli/update-cli/restart-helper.test.ts
+++ b/src/cli/update-cli/restart-helper.test.ts
@@ -98,7 +98,8 @@ describe("restart-helper", () => {
       expect(scriptPath.endsWith(".sh")).toBe(true);
       expect(content).toContain("#!/bin/sh");
       expect(content).toContain("launchctl kickstart -k 'gui/501/ai.openclaw.gateway'");
-      // Should fall back to bootstrap when kickstart fails (service deregistered after bootout)
+      // Should clear disabled state and fall back to bootstrap when kickstart fails.
+      expect(content).toContain("launchctl enable 'gui/501/ai.openclaw.gateway'");
       expect(content).toContain("launchctl bootstrap 'gui/501'");
       expect(content).toContain('rm -f "$0"');
       await cleanupScript(scriptPath);
diff --git a/src/cli/update-cli/restart-helper.ts b/src/cli/update-cli/restart-helper.ts
index 02ac29d03bb..c27f25cdc49 100644
--- a/src/cli/update-cli/restart-helper.ts
+++ b/src/cli/update-cli/restart-helper.ts
@@ -95,8 +95,10 @@ rm -f "$0"
 # Wait briefly to ensure file locks are released after update.
 sleep 1
 # Try kickstart first (works when the service is still registered).
-# If it fails (e.g. after bootout), re-register via bootstrap then kickstart.
+# If it fails (e.g. after bootout), clear any persisted disabled state,
+# then re-register via bootstrap and kickstart.
 if ! launchctl kickstart -k 'gui/${uid}/${escaped}' 2>/dev/null; then
+  launchctl enable 'gui/${uid}/${escaped}' 2>/dev/null
   launchctl bootstrap 'gui/${uid}' '${escapedPlistPath}' 2>/dev/null
   launchctl kickstart -k 'gui/${uid}/${escaped}' 2>/dev/null || true
 fi