diff --git a/src/cli/update-cli/restart-helper.test.ts b/src/cli/update-cli/restart-helper.test.ts
index f00b513edba..b654f5ad425 100644
--- a/src/cli/update-cli/restart-helper.test.ts
+++ b/src/cli/update-cli/restart-helper.test.ts
@@ -75,7 +75,7 @@ exit 0
     const pollAttemptIncrement = "set /a attempts+=1";
     const pollNetstatCheck = `netstat -ano | findstr /R /C:":${port} .*LISTENING" >nul`;
     const forceKillLabel = ":force_kill_listener";
-    const forceKillCommand = "taskkill /F /PID %%P >nul 2>&1";
+    const forceKillCommand = "taskkill /F /PID %%P >>";
     const portReleasedLabel = ":port_released";
     const runCommand = 'schtasks /Run /TN "';
     const endIndex = content.indexOf(endCommand);
@@ -151,7 +151,7 @@ exit 0
       await cleanupScript(scriptPath);
     });
 
-    it("captures macOS launchctl stderr to ~/.openclaw/logs/update-restart.log (#68486)", async () => {
+    it("captures macOS launchctl stderr to ~/.openclaw/logs/gateway-restart.log (#68486)", async () => {
       // Silent failure in macOS update restart helper: previously every
       // launchctl call redirected stderr to /dev/null and the final kickstart
       // was chained with `|| true`, so bootstrap/kickstart failures were
@@ -166,7 +166,7 @@ exit 0
         HOME: "/Users/testuser",
       });
       expect(content).toContain(
-        "exec >>'/Users/testuser/.openclaw/logs/update-restart.log' 2>&1 || true",
+        "exec >>'/Users/testuser/.openclaw/logs/gateway-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.
@@ -187,7 +187,7 @@ exit 0
 
       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",
+        "exec >>'/tmp/openclaw-state/logs/gateway-restart.log' 2>&1 || true",
       );
       await cleanupScript(scriptPath);
     });
@@ -220,13 +220,13 @@ exit 0
       const result = await executeScript(scriptPath, {
         PATH: `${fakeBinDir}:${process.env.PATH ?? ""}`,
       });
-      const log = await fs.readFile(path.join(stateDir, "logs", "update-restart.log"), "utf-8");
+      const log = await fs.readFile(path.join(stateDir, "logs", "gateway-restart.log"), "utf-8");
 
       expect(result.code).toBe(42);
-      expect(log).toContain("openclaw update restart attempt (label=ai.openclaw.gateway)");
+      expect(log).toContain("openclaw restart attempt source=update target=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");
+      expect(log).toContain("openclaw restart failed source=update status=42");
+      expect(log).not.toContain("openclaw restart done source=update");
     });
 
     it("continues the macOS restart path when log setup fails", async () => {
@@ -279,11 +279,11 @@ exit 0
       const result = await executeScript(scriptPath, {
         PATH: `${fakeBinDir}:${process.env.PATH ?? ""}`,
       });
-      const log = await fs.readFile(path.join(stateDir, "logs", "update-restart.log"), "utf-8");
+      const log = await fs.readFile(path.join(stateDir, "logs", "gateway-restart.log"), "utf-8");
 
       expect(result.code).toBeNull();
-      expect(log).toContain("label=ai.openclaw.$(echo injected)");
-      expect(log).not.toContain("label=ai.openclaw.injected");
+      expect(log).toContain("target=ai.openclaw.$(echo injected)");
+      expect(log).not.toContain("target=ai.openclaw.injected");
     });
 
     it("uses OPENCLAW_LAUNCHD_LABEL override on macOS", async () => {
@@ -306,8 +306,10 @@ exit 0
       });
       expect(scriptPath.endsWith(".bat")).toBe(true);
       expect(content).toContain("@echo off");
+      expect(content).toContain("gateway-restart.log");
+      expect(content).toContain("openclaw restart attempt source=update target=OpenClaw Gateway");
       expect(content).toContain('schtasks /End /TN "OpenClaw Gateway"');
-      expect(content).toContain('schtasks /Run /TN "OpenClaw Gateway"');
+      expect(content).toContain('schtasks /Run /TN "OpenClaw Gateway" >>');
       expectWindowsRestartWaitOrdering(content);
       // Batch self-cleanup
       expect(content).toContain('del "%~f0"');
diff --git a/src/cli/update-cli/restart-helper.ts b/src/cli/update-cli/restart-helper.ts
index c2c200ceef2..a2191f7d4ae 100644
--- a/src/cli/update-cli/restart-helper.ts
+++ b/src/cli/update-cli/restart-helper.ts
@@ -2,13 +2,18 @@ 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, resolveStateDir } from "../../config/paths.js";
+import { DEFAULT_GATEWAY_PORT } from "../../config/paths.js";
 import { quoteCmdScriptArg } from "../../daemon/cmd-argv.js";
 import {
   resolveGatewayLaunchAgentLabel,
   resolveGatewaySystemdServiceName,
   resolveGatewayWindowsTaskName,
 } from "../../daemon/constants.js";
+import {
+  renderCmdRestartLogSetup,
+  renderPosixRestartLogSetup,
+  shellEscapeRestartLogValue,
+} from "../../daemon/restart-logs.js";
 import { normalizeOptionalString } from "../../shared/string-coerce.js";
 
 /**
@@ -71,14 +76,24 @@ export async function prepareRestartScript(
     if (platform === "linux") {
       const unitName = resolveSystemdUnit(env);
       const escaped = shellEscape(unitName);
+      const logSetup = renderPosixRestartLogSetup({ ...process.env, ...env });
       filename = `openclaw-restart-${timestamp}.sh`;
       scriptContent = `#!/bin/sh
 # Standalone restart script — survives parent process termination.
 # Wait briefly to ensure file locks are released after update.
 sleep 1
-systemctl --user restart '${escaped}'
+${logSetup}
+printf '[%s] openclaw restart attempt source=update target=%s\\n' "$(date -u +%FT%TZ)" '${escaped}' >&2
+if systemctl --user restart '${escaped}'; then
+  status=0
+  printf '[%s] openclaw restart done source=update\\n' "$(date -u +%FT%TZ)" >&2
+else
+  status=$?
+  printf '[%s] openclaw restart failed source=update status=%s\\n' "$(date -u +%FT%TZ)" "$status" >&2
+fi
 # Self-cleanup
 rm -f "$0"
+exit "$status"
 `;
     } else if (platform === "darwin") {
       const label = resolveLaunchdLabel(env);
@@ -90,10 +105,7 @@ 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 logDir = path.join(resolveStateDir(env), "logs");
-      const logPath = path.join(logDir, "update-restart.log");
-      const escapedLogDir = shellEscape(logDir);
-      const escapedLogPath = shellEscape(logPath);
+      const logSetup = renderPosixRestartLogSetup({ ...process.env, ...env });
       filename = `openclaw-restart-${timestamp}.sh`;
       scriptContent = `#!/bin/sh
 # Standalone restart script — survives parent process termination.
@@ -102,9 +114,8 @@ sleep 1
 # Capture launchctl output so bootstrap/kickstart failures leave a durable
 # audit trail. Log setup is best-effort: restart must still run if the log path
 # is temporarily unavailable.
-mkdir -p '${escapedLogDir}' 2>/dev/null || true
-exec >>'${escapedLogPath}' 2>&1 || true
-printf '[%s] openclaw update restart attempt (label=%s)\\n' "$(date -u +%FT%TZ)" '${escaped}' >&2
+${logSetup}
+printf '[%s] openclaw restart attempt source=update target=%s\\n' "$(date -u +%FT%TZ)" '${shellEscapeRestartLogValue(label)}' >&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. The final status is captured
@@ -117,9 +128,9 @@ if ! launchctl kickstart -k 'gui/${uid}/${escaped}'; then
   status=$?
 fi
 if [ "$status" -eq 0 ]; then
-  printf '[%s] openclaw update restart done\\n' "$(date -u +%FT%TZ)" >&2
+  printf '[%s] openclaw restart done source=update\\n' "$(date -u +%FT%TZ)" >&2
 else
-  printf '[%s] openclaw update restart failed status=%s\\n' "$(date -u +%FT%TZ)" "$status" >&2
+  printf '[%s] openclaw restart failed source=update status=%s\\n' "$(date -u +%FT%TZ)" "$status" >&2
 fi
 # Self-cleanup (log is retained under the OpenClaw state logs directory).
 rm -f "$0"
@@ -132,12 +143,15 @@ exit "$status"
       }
       const port =
         Number.isFinite(gatewayPort) && gatewayPort > 0 ? gatewayPort : DEFAULT_GATEWAY_PORT;
+      const restartLog = renderCmdRestartLogSetup({ ...process.env, ...env });
       filename = `openclaw-restart-${timestamp}.bat`;
       scriptContent = `@echo off
 REM Standalone restart script — survives parent process termination.
 REM Wait briefly to ensure file locks are released after update.
 timeout /t 2 /nobreak >nul
-schtasks /End /TN "${taskName}"
+${restartLog.lines.join("\r\n")}
+>> ${restartLog.quotedLogPath} 2>&1 echo [%DATE% %TIME%] openclaw restart attempt source=update target=${taskName}
+schtasks /End /TN "${taskName}" >> ${restartLog.quotedLogPath} 2>&1
 REM Poll for gateway port release before rerun; force-kill listener if stuck.
 set /a attempts=0
 :wait_for_port_release
@@ -149,13 +163,20 @@ timeout /t 1 /nobreak >nul
 goto wait_for_port_release
 :force_kill_listener
 for /f "tokens=5" %%P in ('netstat -ano ^| findstr /R /C:":${port} .*LISTENING"') do (
-  taskkill /F /PID %%P >nul 2>&1
+  taskkill /F /PID %%P >> ${restartLog.quotedLogPath} 2>&1
   goto port_released
 )
 :port_released
-schtasks /Run /TN "${taskName}"
+schtasks /Run /TN "${taskName}" >> ${restartLog.quotedLogPath} 2>&1
+set "status=%ERRORLEVEL%"
+if not "%status%"=="0" (
+  >> ${restartLog.quotedLogPath} 2>&1 echo [%DATE% %TIME%] openclaw restart failed source=update status=%status%
+) else (
+  >> ${restartLog.quotedLogPath} 2>&1 echo [%DATE% %TIME%] openclaw restart done source=update
+)
 REM Self-cleanup
 del "%~f0"
+exit /b %status%
 `;
     } else {
       return null;
diff --git a/src/daemon/launchd-restart-handoff.test.ts b/src/daemon/launchd-restart-handoff.test.ts
index c469308760c..9293f0f37aa 100644
--- a/src/daemon/launchd-restart-handoff.test.ts
+++ b/src/daemon/launchd-restart-handoff.test.ts
@@ -41,10 +41,13 @@ describe("scheduleDetachedLaunchdRestartHandoff", () => {
     expect(args[6]).toBe("9876");
     expect(args[7]).toBe("ai.openclaw.gateway");
     expect(args[1]).toContain('while kill -0 "$wait_pid" >/dev/null 2>&1; do');
-    expect(args[1]).toContain('launchctl enable "$service_target" >/dev/null 2>&1');
     expect(args[1]).toContain(
-      'if ! launchctl kickstart -k "$service_target" >/dev/null 2>&1; then',
+      "exec >>'/Users/test/.openclaw/logs/gateway-restart.log' 2>&1 || true",
     );
+    expect(args[1]).toContain("openclaw restart attempt source=launchd-handoff mode=kickstart");
+    expect(args[1]).toContain('launchctl enable "$service_target"');
+    expect(args[1]).toContain('if launchctl kickstart -k "$service_target"; then');
+    expect(args[1]).not.toMatch(/launchctl[^\n]*\/dev\/null/);
     expect(args[1]).not.toContain("sleep 1");
     expect(unrefMock).toHaveBeenCalledTimes(1);
   });
@@ -62,7 +65,7 @@ describe("scheduleDetachedLaunchdRestartHandoff", () => {
 
     const [, args] = spawnMock.mock.calls[0] as [string, string[]];
     expect(args[7]).toBe("ai.openclaw.gateway");
-    expect(args[1]).toContain('launchctl start "$label" >/dev/null 2>&1');
+    expect(args[1]).toContain('if launchctl start "$label"; then');
     expect(args[1]).not.toContain('basename "$service_target"');
   });
 
diff --git a/src/daemon/launchd-restart-handoff.ts b/src/daemon/launchd-restart-handoff.ts
index c26327ab94a..ed709a13f21 100644
--- a/src/daemon/launchd-restart-handoff.ts
+++ b/src/daemon/launchd-restart-handoff.ts
@@ -5,6 +5,7 @@ import { formatErrorMessage } from "../infra/errors.js";
 import { normalizeOptionalString } from "../shared/string-coerce.js";
 import { sanitizeForLog } from "../terminal/ansi.js";
 import { resolveGatewayLaunchAgentLabel } from "./constants.js";
+import { renderPosixRestartLogSetup } from "./restart-logs.js";
 
 export type LaunchdRestartHandoffMode = "kickstart" | "start-after-exit";
 
@@ -74,9 +75,14 @@ export function isCurrentProcessLaunchdServiceLabel(
   return Boolean(configuredLabel && configuredLabel === label);
 }
 
-function buildLaunchdRestartScript(mode: LaunchdRestartHandoffMode): string {
+function buildLaunchdRestartScript(
+  mode: LaunchdRestartHandoffMode,
+  env: Record<string, string | undefined>,
+): string {
   const waitForCallerPid = `wait_pid="$4"
 label="$5"
+${renderPosixRestartLogSetup(env)}
+printf '[%s] openclaw restart attempt source=launchd-handoff mode=${mode} target=%s waitPid=%s\\n' "$(date -u +%FT%TZ)" "$service_target" "$wait_pid" >&2
 if [ -n "$wait_pid" ] && [ "$wait_pid" -gt 1 ] 2>/dev/null; then
   while kill -0 "$wait_pid" >/dev/null 2>&1; do
     sleep 0.1
@@ -90,12 +96,23 @@ fi
 domain="$2"
 plist_path="$3"
 ${waitForCallerPid}
-launchctl enable "$service_target" >/dev/null 2>&1
-if ! launchctl kickstart -k "$service_target" >/dev/null 2>&1; then
-  if launchctl bootstrap "$domain" "$plist_path" >/dev/null 2>&1; then
-    launchctl kickstart -k "$service_target" >/dev/null 2>&1 || true
+status=0
+launchctl enable "$service_target"
+if launchctl kickstart -k "$service_target"; then
+  status=0
+else
+  status=$?
+  if launchctl bootstrap "$domain" "$plist_path"; then
+    launchctl kickstart -k "$service_target"
+    status=$?
   fi
 fi
+if [ "$status" -eq 0 ]; then
+  printf '[%s] openclaw restart done source=launchd-handoff mode=${mode}\\n' "$(date -u +%FT%TZ)" >&2
+else
+  printf '[%s] openclaw restart failed source=launchd-handoff mode=${mode} status=%s\\n' "$(date -u +%FT%TZ)" "$status" >&2
+fi
+exit "$status"
 `;
   }
 
@@ -104,14 +121,30 @@ fi
 domain="$2"
 plist_path="$3"
 ${waitForCallerPid}
-launchctl enable "$service_target" >/dev/null 2>&1
-if ! launchctl start "$label" >/dev/null 2>&1; then
-  if launchctl bootstrap "$domain" "$plist_path" >/dev/null 2>&1; then
-    launchctl start "$label" >/dev/null 2>&1 || launchctl kickstart -k "$service_target" >/dev/null 2>&1 || true
+status=0
+launchctl enable "$service_target"
+if launchctl start "$label"; then
+  status=0
+else
+  status=$?
+  if launchctl bootstrap "$domain" "$plist_path"; then
+    if launchctl start "$label"; then
+      status=0
+    else
+      launchctl kickstart -k "$service_target"
+      status=$?
+    fi
   else
-    launchctl kickstart -k "$service_target" >/dev/null 2>&1 || true
+    launchctl kickstart -k "$service_target"
+    status=$?
   fi
 fi
+if [ "$status" -eq 0 ]; then
+  printf '[%s] openclaw restart done source=launchd-handoff mode=${mode}\\n' "$(date -u +%FT%TZ)" >&2
+else
+  printf '[%s] openclaw restart failed source=launchd-handoff mode=${mode} status=%s\\n' "$(date -u +%FT%TZ)" "$status" >&2
+fi
+exit "$status"
 `;
 }
 
@@ -125,12 +158,13 @@ export function scheduleDetachedLaunchdRestartHandoff(params: {
     typeof params.waitForPid === "number" && Number.isFinite(params.waitForPid)
       ? Math.floor(params.waitForPid)
       : 0;
+  const restartEnv = { ...process.env, ...params.env };
   try {
     const child = spawn(
       "/bin/sh",
       [
         "-c",
-        buildLaunchdRestartScript(params.mode),
+        buildLaunchdRestartScript(params.mode, restartEnv),
         "openclaw-launchd-restart-handoff",
         target.serviceTarget,
         target.domain,
@@ -141,7 +175,7 @@ export function scheduleDetachedLaunchdRestartHandoff(params: {
       {
         detached: true,
         stdio: "ignore",
-        env: { ...process.env, ...params.env },
+        env: restartEnv,
       },
     );
     child.unref();
diff --git a/src/infra/windows-task-restart.test.ts b/src/infra/windows-task-restart.test.ts
index 91a5cc1e216..ed64a6fc10e 100644
--- a/src/infra/windows-task-restart.test.ts
+++ b/src/infra/windows-task-restart.test.ts
@@ -113,7 +113,11 @@ describe("relaunchGatewayScheduledTask", () => {
     expect(scriptPath).toBeTruthy();
     const script = fs.readFileSync(scriptPath, "utf8");
     expect(script).toContain("timeout /t 1 /nobreak >nul");
-    expect(script).toContain('schtasks /Run /TN "OpenClaw Gateway (work)" >nul 2>&1');
+    expect(script).toContain("gateway-restart.log");
+    expect(script).toContain(
+      'openclaw restart attempt source=windows-task-handoff target="OpenClaw Gateway (work)"',
+    );
+    expect(script).toContain('schtasks /Run /TN "OpenClaw Gateway (work)" >>');
     expect(script).toContain('del "%~f0" >nul 2>&1');
   });
 
@@ -130,7 +134,7 @@ describe("relaunchGatewayScheduledTask", () => {
 
     const scriptPath = [...createdScriptPaths][0];
     const script = fs.readFileSync(scriptPath, "utf8");
-    expect(script).toContain('schtasks /Run /TN "OpenClaw Gateway (custom)" >nul 2>&1');
+    expect(script).toContain('schtasks /Run /TN "OpenClaw Gateway (custom)" >>');
   });
 
   it("returns failed when the helper cannot be spawned", () => {
diff --git a/src/infra/windows-task-restart.ts b/src/infra/windows-task-restart.ts
index 9709fa93d06..8a1db004c49 100644
--- a/src/infra/windows-task-restart.ts
+++ b/src/infra/windows-task-restart.ts
@@ -4,6 +4,7 @@ import fs from "node:fs";
 import path from "node:path";
 import { quoteCmdScriptArg } from "../daemon/cmd-argv.js";
 import { resolveGatewayWindowsTaskName } from "../daemon/constants.js";
+import { renderCmdRestartLogSetup } from "../daemon/restart-logs.js";
 import { resolveTaskScriptPath } from "../daemon/schtasks.js";
 import { formatErrorMessage } from "./errors.js";
 import type { RestartAttempt } from "./restart.types.js";
@@ -20,28 +21,41 @@ function resolveWindowsTaskName(env: NodeJS.ProcessEnv): string {
   return resolveGatewayWindowsTaskName(env.OPENCLAW_PROFILE);
 }
 
-function buildScheduledTaskRestartScript(taskName: string, taskScriptPath?: string): string {
+function buildScheduledTaskRestartScript(params: {
+  quotedLogPath: string;
+  setupLines: string[];
+  taskName: string;
+  taskScriptPath?: string;
+}): string {
+  const { quotedLogPath, setupLines, taskName, taskScriptPath } = params;
   const quotedTaskName = quoteCmdScriptArg(taskName);
   const lines = [
     "@echo off",
     "setlocal",
-    `schtasks /Query /TN ${quotedTaskName} >nul 2>&1`,
+    ...setupLines,
+    `>> ${quotedLogPath} 2>&1 echo [%DATE% %TIME%] openclaw restart attempt source=windows-task-handoff target=${quotedTaskName}`,
+    `schtasks /Query /TN ${quotedTaskName} >> ${quotedLogPath} 2>&1`,
     "if errorlevel 1 goto fallback",
     "set /a attempts=0",
     ":retry",
     `timeout /t ${TASK_RESTART_RETRY_DELAY_SEC} /nobreak >nul`,
     "set /a attempts+=1",
-    `schtasks /Run /TN ${quotedTaskName} >nul 2>&1`,
+    `schtasks /Run /TN ${quotedTaskName} >> ${quotedLogPath} 2>&1`,
     "if not errorlevel 1 goto cleanup",
     `if %attempts% GEQ ${TASK_RESTART_RETRY_LIMIT} goto fallback`,
     "goto retry",
     ":fallback",
+    `>> ${quotedLogPath} 2>&1 echo [%DATE% %TIME%] openclaw restart fallback source=windows-task-handoff`,
   ];
   if (taskScriptPath) {
     const quotedScript = quoteCmdScriptArg(taskScriptPath);
     lines.push(`if exist ${quotedScript} (`, `  start "" /min cmd.exe /d /c ${quotedScript}`, ")");
   }
-  lines.push(":cleanup", 'del "%~f0" >nul 2>&1');
+  lines.push(
+    ":cleanup",
+    `>> ${quotedLogPath} 2>&1 echo [%DATE% %TIME%] openclaw restart finished source=windows-task-handoff`,
+    'del "%~f0" >nul 2>&1',
+  );
   return lines.join("\r\n");
 }
 
@@ -53,10 +67,16 @@ export function relaunchGatewayScheduledTask(env: NodeJS.ProcessEnv = process.en
     `openclaw-schtasks-restart-${randomUUID()}.cmd`,
   );
   const quotedScriptPath = quoteCmdScriptArg(scriptPath);
+  const restartLog = renderCmdRestartLogSetup({ ...process.env, ...env });
   try {
     fs.writeFileSync(
       scriptPath,
-      `${buildScheduledTaskRestartScript(taskName, taskScriptPath)}\r\n`,
+      `${buildScheduledTaskRestartScript({
+        quotedLogPath: restartLog.quotedLogPath,
+        setupLines: restartLog.lines,
+        taskName,
+        taskScriptPath,
+      })}\r\n`,
       "utf8",
     );
     const child = spawn("cmd.exe", ["/d", "/s", "/c", quotedScriptPath], {