diff --git a/CHANGELOG.md b/CHANGELOG.md
index 592fa8c5a55..8679be724b8 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -68,6 +68,7 @@ Docs: https://docs.openclaw.ai
 - Slack/threads: log failed thread starter and history fetches at verbose level while preserving best-effort fallback behavior, so missing Slack thread context is diagnosable without interrupting inbound handling. (#68594) Thanks @martingarramon.
 - Gateway/restart: keep stale-gateway cleanup from terminating the current process's parent or ancestors, so plugin sidecars like WeChat no longer kill the active gateway and trigger an infinite supervisor restart loop. Fixes #68451. (#68517) Thanks @openperf.
 - Gateway/auth: reject gateway auth credentials that match published example placeholders at startup and secret reload, and keep cloud install snippets from publishing copy-paste gateway/keyring secrets. (#68404) Thanks @coygeek.
+- CLI/update: preserve macOS restart helper launchctl failures in the update restart log without letting log setup block the restart path. (#68492) Thanks @hclsys.
 
 ## 2026.4.15
 
diff --git a/src/cli/update-cli/restart-helper.test.ts b/src/cli/update-cli/restart-helper.test.ts
index 5cbb075036e..f00b513edba 100644
--- a/src/cli/update-cli/restart-helper.test.ts
+++ b/src/cli/update-cli/restart-helper.test.ts
@@ -1,5 +1,7 @@
-import { spawn, type ChildProcess } from "node:child_process";
+import { execFile, spawn, type ChildProcess } from "node:child_process";
 import fs from "node:fs/promises";
+import os from "node:os";
+import path from "node:path";
 import { describe, it, expect, vi, beforeEach, afterEach } from "vitest";
 import { prepareRestartScript, runRestartScript } from "./restart-helper.js";
 
@@ -25,7 +27,45 @@ describe("restart-helper", () => {
   }
 
   async function cleanupScript(scriptPath: string) {
-    await fs.unlink(scriptPath);
+    await fs.unlink(scriptPath).catch((error: unknown) => {
+      if ((error as NodeJS.ErrnoException).code !== "ENOENT") {
+        throw error;
+      }
+    });
+  }
+
+  async function makeTempDir(prefix: string) {
+    return await fs.mkdtemp(path.join(os.tmpdir(), prefix));
+  }
+
+  async function writeFakeLaunchctl(
+    fakeBinDir: string,
+    content = `#!/bin/sh
+echo "launchctl $*" >&2
+case "$1" in
+  kickstart) exit 0 ;;
+  enable|bootstrap) exit 0 ;;
+esac
+exit 0
+`,
+  ) {
+    const launchctlPath = path.join(fakeBinDir, "launchctl");
+    await fs.writeFile(launchctlPath, content, { mode: 0o755 });
+  }
+
+  async function executeScript(scriptPath: string, env: Record<string, string>) {
+    return await new Promise<{ code: number | null; stdout: string; stderr: string }>((resolve) => {
+      execFile(
+        "/bin/sh",
+        [scriptPath],
+        { env: { ...process.env, ...env } },
+        (error, stdout, stderr) => {
+          const execError = error as (Error & { code?: number | string }) | null;
+          const code = typeof execError?.code === "number" ? execError.code : null;
+          resolve({ code, stdout, stderr });
+        },
+      );
+    });
   }
 
   function expectWindowsRestartWaitOrdering(content: string, port = 18789) {
@@ -125,14 +165,127 @@ describe("restart-helper", () => {
         OPENCLAW_PROFILE: "default",
         HOME: "/Users/testuser",
       });
-      expect(content).toContain("exec 2>>'/Users/testuser/.openclaw/logs/update-restart.log'");
-      // Every launchctl call should allow stderr through now (no `2>/dev/null`)
+      expect(content).toContain(
+        "exec >>'/Users/testuser/.openclaw/logs/update-restart.log' 2>&1 || true",
+      );
+      // Every launchctl call should allow output through now (no `2>/dev/null`)
       // and the final kickstart must not swallow its exit code.
       expect(content).not.toMatch(/launchctl[^\n]*2>\/dev\/null/);
       expect(content).not.toMatch(/launchctl kickstart[^\n]*\|\| true/);
       await cleanupScript(scriptPath);
     });
 
+    it("uses OPENCLAW_STATE_DIR for the macOS update restart log", async () => {
+      Object.defineProperty(process, "platform", { value: "darwin" });
+      process.getuid = () => 501;
+
+      const { scriptPath, content } = await prepareAndReadScript({
+        OPENCLAW_PROFILE: "default",
+        HOME: "/Users/testuser",
+        OPENCLAW_STATE_DIR: "/tmp/openclaw-state",
+      });
+
+      expect(content).toContain("mkdir -p '/tmp/openclaw-state/logs' 2>/dev/null || true");
+      expect(content).toContain(
+        "exec >>'/tmp/openclaw-state/logs/update-restart.log' 2>&1 || true",
+      );
+      await cleanupScript(scriptPath);
+    });
+
+    it("returns the final macOS launchctl kickstart failure after logging cleanup", async () => {
+      Object.defineProperty(process, "platform", { value: "darwin" });
+      process.getuid = () => 501;
+      const tmpDir = await makeTempDir("openclaw-restart-helper-");
+      const fakeBinDir = path.join(tmpDir, "bin");
+      const stateDir = path.join(tmpDir, "state");
+      await fs.mkdir(fakeBinDir, { recursive: true });
+      await writeFakeLaunchctl(
+        fakeBinDir,
+        `#!/bin/sh
+echo "launchctl $*" >&2
+case "$1" in
+  kickstart) exit 42 ;;
+  enable|bootstrap) exit 0 ;;
+esac
+exit 0
+`,
+      );
+
+      const { scriptPath } = await prepareAndReadScript({
+        OPENCLAW_PROFILE: "default",
+        HOME: path.join(tmpDir, "home"),
+        OPENCLAW_STATE_DIR: stateDir,
+      });
+
+      const result = await executeScript(scriptPath, {
+        PATH: `${fakeBinDir}:${process.env.PATH ?? ""}`,
+      });
+      const log = await fs.readFile(path.join(stateDir, "logs", "update-restart.log"), "utf-8");
+
+      expect(result.code).toBe(42);
+      expect(log).toContain("openclaw update restart attempt (label=ai.openclaw.gateway)");
+      expect(log).toContain("launchctl kickstart -k gui/501/ai.openclaw.gateway");
+      expect(log).toContain("openclaw update restart failed status=42");
+      expect(log).not.toContain("openclaw update restart done");
+    });
+
+    it("continues the macOS restart path when log setup fails", async () => {
+      Object.defineProperty(process, "platform", { value: "darwin" });
+      process.getuid = () => 501;
+      const tmpDir = await makeTempDir("openclaw-restart-helper-");
+      const fakeBinDir = path.join(tmpDir, "bin");
+      const stateFile = path.join(tmpDir, "state-file");
+      const markerPath = path.join(tmpDir, "launchctl-ran");
+      await fs.mkdir(fakeBinDir, { recursive: true });
+      await fs.writeFile(stateFile, "not a directory");
+      await writeFakeLaunchctl(
+        fakeBinDir,
+        `#!/bin/sh
+printf ran > "$LAUNCHCTL_MARKER"
+exit 0
+`,
+      );
+
+      const { scriptPath } = await prepareAndReadScript({
+        OPENCLAW_PROFILE: "default",
+        HOME: path.join(tmpDir, "home"),
+        OPENCLAW_STATE_DIR: stateFile,
+      });
+
+      const result = await executeScript(scriptPath, {
+        LAUNCHCTL_MARKER: markerPath,
+        PATH: `${fakeBinDir}:${process.env.PATH ?? ""}`,
+      });
+
+      expect(result.code).toBeNull();
+      await expect(fs.readFile(markerPath, "utf-8")).resolves.toBe("ran");
+    });
+
+    it("logs custom macOS launchd labels without shell expansion", async () => {
+      Object.defineProperty(process, "platform", { value: "darwin" });
+      process.getuid = () => 501;
+      const tmpDir = await makeTempDir("openclaw-restart-helper-");
+      const fakeBinDir = path.join(tmpDir, "bin");
+      const stateDir = path.join(tmpDir, "state");
+      await fs.mkdir(fakeBinDir, { recursive: true });
+      await writeFakeLaunchctl(fakeBinDir);
+
+      const { scriptPath } = await prepareAndReadScript({
+        OPENCLAW_LAUNCHD_LABEL: "ai.openclaw.$(echo injected)",
+        HOME: path.join(tmpDir, "home"),
+        OPENCLAW_STATE_DIR: stateDir,
+      });
+
+      const result = await executeScript(scriptPath, {
+        PATH: `${fakeBinDir}:${process.env.PATH ?? ""}`,
+      });
+      const log = await fs.readFile(path.join(stateDir, "logs", "update-restart.log"), "utf-8");
+
+      expect(result.code).toBeNull();
+      expect(log).toContain("label=ai.openclaw.$(echo injected)");
+      expect(log).not.toContain("label=ai.openclaw.injected");
+    });
+
     it("uses OPENCLAW_LAUNCHD_LABEL override on macOS", async () => {
       Object.defineProperty(process, "platform", { value: "darwin" });
       process.getuid = () => 501;
diff --git a/src/cli/update-cli/restart-helper.ts b/src/cli/update-cli/restart-helper.ts
index 934c2b4b9ea..c2c200ceef2 100644
--- a/src/cli/update-cli/restart-helper.ts
+++ b/src/cli/update-cli/restart-helper.ts
@@ -2,7 +2,7 @@ import { spawn } from "node:child_process";
 import fs from "node:fs/promises";
 import os from "node:os";
 import path from "node:path";
-import { DEFAULT_GATEWAY_PORT } from "../../config/paths.js";
+import { DEFAULT_GATEWAY_PORT, resolveStateDir } from "../../config/paths.js";
 import { quoteCmdScriptArg } from "../../daemon/cmd-argv.js";
 import {
   resolveGatewayLaunchAgentLabel,
@@ -90,34 +90,40 @@ rm -f "$0"
       const home = normalizeOptionalString(env.HOME) || process.env.HOME || os.homedir();
       const plistPath = path.join(home, "Library", "LaunchAgents", `${label}.plist`);
       const escapedPlistPath = shellEscape(plistPath);
-      const logPath = path.join(home, ".openclaw", "logs", "update-restart.log");
+      const logDir = path.join(resolveStateDir(env), "logs");
+      const logPath = path.join(logDir, "update-restart.log");
+      const escapedLogDir = shellEscape(logDir);
       const escapedLogPath = shellEscape(logPath);
       filename = `openclaw-restart-${timestamp}.sh`;
       scriptContent = `#!/bin/sh
 # Standalone restart script — survives parent process termination.
 # Wait briefly to ensure file locks are released after update.
 sleep 1
-# Capture launchctl stderr so bootstrap/kickstart failures leave a durable
-# audit trail. Without this, transient launchctl errors (plist-on-disk race,
-# schema rejection, stale job) disappear into /dev/null and the updater
-# reports success while the gateway is silently offline — see #68486.
-mkdir -p "$(dirname '${escapedLogPath}')" 2>/dev/null || true
-exec 2>>'${escapedLogPath}'
-echo "[$(date -u +%FT%TZ)] openclaw update restart attempt (label=${escaped})" >&2
+# Capture launchctl output so bootstrap/kickstart failures leave a durable
+# audit trail. Log setup is best-effort: restart must still run if the log path
+# is temporarily unavailable.
+mkdir -p '${escapedLogDir}' 2>/dev/null || true
+exec >>'${escapedLogPath}' 2>&1 || true
+printf '[%s] openclaw update restart attempt (label=%s)\\n' "$(date -u +%FT%TZ)" '${escaped}' >&2
 # Try kickstart first (works when the service is still registered).
 # If it fails (e.g. after bootout), clear any persisted disabled state,
-# then re-register via bootstrap and kickstart. Any step's stderr now
-# lands in update-restart.log; the final kickstart no longer swallows
-# its exit code with \`|| true\`, so a genuine failure exits non-zero and
-# is inspectable.
+# then re-register via bootstrap and kickstart. The final status is captured
+# before self-cleanup so a genuine failure remains observable.
+status=0
 if ! launchctl kickstart -k 'gui/${uid}/${escaped}'; then
   launchctl enable 'gui/${uid}/${escaped}'
   launchctl bootstrap 'gui/${uid}' '${escapedPlistPath}'
   launchctl kickstart -k 'gui/${uid}/${escaped}'
+  status=$?
 fi
-echo "[$(date -u +%FT%TZ)] openclaw update restart done" >&2
-# Self-cleanup (log is retained under ~/.openclaw/logs/update-restart.log).
+if [ "$status" -eq 0 ]; then
+  printf '[%s] openclaw update restart done\\n' "$(date -u +%FT%TZ)" >&2
+else
+  printf '[%s] openclaw update restart failed status=%s\\n' "$(date -u +%FT%TZ)" "$status" >&2
+fi
+# Self-cleanup (log is retained under the OpenClaw state logs directory).
 rm -f "$0"
+exit "$status"
 `;
     } else if (platform === "win32") {
       const taskName = resolveWindowsTaskName(env);