diff --git a/src/cli/update-cli.ts b/src/cli/update-cli.ts
index 9610f41ba..6f893f8cd 100644
--- a/src/cli/update-cli.ts
+++ b/src/cli/update-cli.ts
@@ -42,6 +42,28 @@ const STEP_LABELS: Record<string, string> = {
 type UpdateChannel = "stable" | "beta";
 
 const DEFAULT_UPDATE_CHANNEL: UpdateChannel = "stable";
+const UPDATE_QUIPS = [
+  "Leveled up! New skills unlocked. You're welcome.",
+  "Fresh code, same lobster. Miss me?",
+  "Back and better. Did you even notice I was gone?",
+  "Update complete. I learned some new tricks while I was out.",
+  "Upgraded! Now with 23% more sass.",
+  "I've evolved. Try to keep up.",
+  "New version, who dis? Oh right, still me but shinier.",
+  "Patched, polished, and ready to pinch. Let's go.",
+  "The lobster has molted. Harder shell, sharper claws.",
+  "Update done! Check the changelog or just trust me, it's good.",
+  "Reborn from the boiling waters of npm. Stronger now.",
+  "I went away and came back smarter. You should try it sometime.",
+  "Update complete. The bugs feared me, so they left.",
+  "New version installed. Old version sends its regards.",
+  "Firmware fresh. Brain wrinkles: increased.",
+  "I've seen things you wouldn't believe. Anyway, I'm updated.",
+  "Back online. The changelog is long but our friendship is longer.",
+  "Upgraded! Peter fixed stuff. Blame him if it breaks.",
+  "Molting complete. Please don't look at my soft shell phase.",
+  "Version bump! Same chaos energy, fewer crashes (probably).",
+];
 
 function normalizeChannel(value?: string | null): UpdateChannel | null {
   if (!value) return null;
@@ -61,6 +83,10 @@ function channelToTag(channel: UpdateChannel): string {
   return channel === "beta" ? "beta" : "latest";
 }
 
+function pickUpdateQuip(): string {
+  return UPDATE_QUIPS[Math.floor(Math.random() * UPDATE_QUIPS.length)] ?? "Update complete.";
+}
+
 function normalizeVersionTag(tag: string): string | null {
   const trimmed = tag.trim();
   if (!trimmed) return null;
@@ -402,6 +428,10 @@ export async function updateCommand(opts: UpdateCommandOptions): Promise<void> {
       );
     }
   }
+
+  if (!opts.json) {
+    defaultRuntime.log(theme.muted(pickUpdateQuip()));
+  }
 }
 
 export function registerUpdateCli(program: Command) {
diff --git a/src/commands/configure.daemon.ts b/src/commands/configure.daemon.ts
index 465ee3731..d713327f9 100644
--- a/src/commands/configure.daemon.ts
+++ b/src/commands/configure.daemon.ts
@@ -72,6 +72,7 @@ export async function maybeInstallDaemon(params: {
   }
 
   if (shouldInstall) {
+    let installError: unknown | null = null;
     await withProgress(
       { label: "Gateway daemon", indeterminate: true, delayMs: 0 },
       async (progress) => {
@@ -117,16 +118,33 @@ export async function maybeInstallDaemon(params: {
         });
 
         progress.setLabel("Installing Gateway daemon…");
-        await service.install({
-          env: process.env,
-          stdout: process.stdout,
-          programArguments,
-          workingDirectory,
-          environment,
-        });
-        progress.setLabel("Gateway daemon installed.");
+        try {
+          await service.install({
+            env: process.env,
+            stdout: process.stdout,
+            programArguments,
+            workingDirectory,
+            environment,
+          });
+          progress.setLabel("Gateway daemon installed.");
+        } catch (err) {
+          installError = err;
+          progress.setLabel("Gateway daemon install failed.");
+        }
       },
     );
+    if (installError) {
+      note(`Gateway daemon install failed: ${String(installError)}`, "Gateway");
+      if (process.platform === "win32") {
+        note(
+          "Tip: rerun from an elevated PowerShell (Start → type PowerShell → right-click → Run as administrator) or skip daemon install.",
+          "Gateway",
+        );
+      } else {
+        note("Tip: rerun `clawdbot daemon install` after fixing the error.", "Gateway");
+      }
+      return;
+    }
     shouldCheckLinger = true;
   }
 
diff --git a/src/commands/onboard-non-interactive/local/daemon-install.ts b/src/commands/onboard-non-interactive/local/daemon-install.ts
index 82b14d705..b0f1497e3 100644
--- a/src/commands/onboard-non-interactive/local/daemon-install.ts
+++ b/src/commands/onboard-non-interactive/local/daemon-install.ts
@@ -69,12 +69,24 @@ export async function installGatewayDaemonNonInteractive(params: {
         ? resolveGatewayLaunchAgentLabel(process.env.CLAWDBOT_PROFILE)
         : undefined,
   });
-  await service.install({
-    env: process.env,
-    stdout: process.stdout,
-    programArguments,
-    workingDirectory,
-    environment,
-  });
+  try {
+    await service.install({
+      env: process.env,
+      stdout: process.stdout,
+      programArguments,
+      workingDirectory,
+      environment,
+    });
+  } catch (err) {
+    runtime.error(`Gateway daemon install failed: ${String(err)}`);
+    if (process.platform === "win32") {
+      runtime.log(
+        "Tip: rerun from an elevated PowerShell (Start → type PowerShell → right-click → Run as administrator) or skip daemon install.",
+      );
+    } else {
+      runtime.log("Tip: rerun `clawdbot daemon install` after fixing the error.");
+    }
+    return;
+  }
   await ensureSystemdUserLingerNonInteractive({ runtime });
 }
diff --git a/src/daemon/schtasks.ts b/src/daemon/schtasks.ts
index a260f078a..2631e5b83 100644
--- a/src/daemon/schtasks.ts
+++ b/src/daemon/schtasks.ts
@@ -26,6 +26,15 @@ function quoteCmdArg(value: string): string {
   return `"${value.replace(/"/g, '\\"')}"`;
 }
 
+function resolveTaskUser(env: Record<string, string | undefined>): string | null {
+  const username = env.USERNAME || env.USER || env.LOGNAME;
+  if (!username) return null;
+  if (username.includes("\\")) return username;
+  const domain = env.USERDOMAIN;
+  if (domain) return `${domain}\\${username}`;
+  return username;
+}
+
 function parseCommandLine(value: string): string[] {
   const args: string[] = [];
   let current = "";
@@ -216,7 +225,7 @@ export async function installScheduledTask({
 
   const taskName = resolveGatewayWindowsTaskName(env.CLAWDBOT_PROFILE);
   const quotedScript = quoteCmdArg(scriptPath);
-  const create = await execSchtasks([
+  const baseArgs = [
     "/Create",
     "/F",
     "/SC",
@@ -227,9 +236,20 @@ export async function installScheduledTask({
     taskName,
     "/TR",
     quotedScript,
-  ]);
+  ];
+  const taskUser = resolveTaskUser(env);
+  let create = await execSchtasks(
+    taskUser ? [...baseArgs, "/RU", taskUser, "/NP", "/IT"] : baseArgs,
+  );
+  if (create.code !== 0 && taskUser) {
+    create = await execSchtasks(baseArgs);
+  }
   if (create.code !== 0) {
-    throw new Error(`schtasks create failed: ${create.stderr || create.stdout}`.trim());
+    const detail = create.stderr || create.stdout;
+    const hint = /access is denied/i.test(detail)
+      ? " Run PowerShell as Administrator or rerun without installing the daemon."
+      : "";
+    throw new Error(`schtasks create failed: ${detail}${hint}`.trim());
   }
 
   await execSchtasks(["/Run", "/TN", taskName]);