diff --git a/src/commands/configure.ts b/src/commands/configure.ts
index 8ab618a62..e7229c9ac 100644
--- a/src/commands/configure.ts
+++ b/src/commands/configure.ts
@@ -67,6 +67,7 @@ import {
   GOOGLE_GEMINI_DEFAULT_MODEL,
 } from "./google-gemini-model-default.js";
 import { healthCommand } from "./health.js";
+import { formatHealthCheckFailure } from "./health-format.js";
 import {
   applyAuthProfileConfig,
   applyMinimaxConfig,
@@ -1286,7 +1287,7 @@ export async function runConfigureWizard(
     try {
       await healthCommand({ json: false, timeoutMs: 10_000 }, runtime);
     } catch (err) {
-      runtime.error(`Health check failed: ${String(err)}`);
+      runtime.error(formatHealthCheckFailure(err));
       note(
         [
           "Docs:",
diff --git a/src/commands/doctor.ts b/src/commands/doctor.ts
index 64807b20b..291605014 100644
--- a/src/commands/doctor.ts
+++ b/src/commands/doctor.ts
@@ -80,6 +80,7 @@ import {
   shouldSuggestMemorySystem,
 } from "./doctor-workspace.js";
 import { healthCommand } from "./health.js";
+import { formatHealthCheckFailure } from "./health-format.js";
 import { applyWizardMetadata, printWizardHeader } from "./onboard-helpers.js";
 import { ensureSystemdUserLingerInteractive } from "./systemd-linger.js";
 
@@ -310,7 +311,7 @@ export async function doctorCommand(
       note("Gateway not running.", "Gateway");
       note(gatewayDetails.message, "Gateway connection");
     } else {
-      runtime.error(`Health check failed: ${message}`);
+      runtime.error(formatHealthCheckFailure(err));
     }
   }
 
@@ -455,7 +456,7 @@ export async function doctorCommand(
               note("Gateway not running.", "Gateway");
               note(gatewayDetails.message, "Gateway connection");
             } else {
-              runtime.error(`Health check failed: ${message}`);
+              runtime.error(formatHealthCheckFailure(err));
             }
           }
         }
diff --git a/src/commands/health-format.test.ts b/src/commands/health-format.test.ts
new file mode 100644
index 000000000..a0cd88322
--- /dev/null
+++ b/src/commands/health-format.test.ts
@@ -0,0 +1,43 @@
+import { describe, expect, it } from "vitest";
+
+import { formatHealthCheckFailure } from "./health-format.js";
+
+const stripAnsi = (input: string) =>
+  input.replace(
+    // biome-ignore lint/suspicious/noControlCharactersInRegex: strip ANSI escape sequences
+    /\u001b\[[0-9;]*m/g,
+    "",
+  );
+
+describe("formatHealthCheckFailure", () => {
+  it("keeps non-rich output stable", () => {
+    const err = new Error(
+      "gateway closed (1006 abnormal closure): no close reason",
+    );
+    expect(formatHealthCheckFailure(err, { rich: false })).toBe(
+      `Health check failed: ${String(err)}`,
+    );
+  });
+
+  it("formats gateway connection details as indented key/value lines", () => {
+    const err = new Error(
+      [
+        "gateway closed (1006 abnormal closure (no close frame)): no close reason",
+        "Gateway target: ws://127.0.0.1:19001",
+        "Source: local loopback",
+        "Config: /Users/steipete/.clawdbot-dev/clawdbot.json",
+        "Bind: loopback",
+      ].join("\n"),
+    );
+
+    expect(stripAnsi(formatHealthCheckFailure(err, { rich: true }))).toBe(
+      [
+        "Health check failed: gateway closed (1006 abnormal closure (no close frame)): no close reason",
+        "  Gateway target: ws://127.0.0.1:19001",
+        "  Source: local loopback",
+        "  Config: /Users/steipete/.clawdbot-dev/clawdbot.json",
+        "  Bind: loopback",
+      ].join("\n"),
+    );
+  });
+});
diff --git a/src/commands/health-format.ts b/src/commands/health-format.ts
new file mode 100644
index 000000000..81dfa8f8e
--- /dev/null
+++ b/src/commands/health-format.ts
@@ -0,0 +1,48 @@
+import { colorize, isRich, theme } from "../terminal/theme.js";
+
+const formatKv = (line: string, rich: boolean) => {
+  const idx = line.indexOf(": ");
+  if (idx <= 0) return colorize(rich, theme.muted, line);
+  const key = line.slice(0, idx);
+  const value = line.slice(idx + 2);
+
+  const valueColor =
+    key === "Gateway target" || key === "Config"
+      ? theme.command
+      : key === "Source"
+        ? theme.muted
+        : theme.info;
+
+  return `${colorize(rich, theme.muted, `${key}:`)} ${colorize(rich, valueColor, value)}`;
+};
+
+export function formatHealthCheckFailure(
+  err: unknown,
+  opts: { rich?: boolean } = {},
+): string {
+  const rich = opts.rich ?? isRich();
+  const raw = String(err);
+  const message = err instanceof Error ? err.message : raw;
+
+  if (!rich) return `Health check failed: ${raw}`;
+
+  const lines = message
+    .split("\n")
+    .map((l) => l.trimEnd())
+    .filter(Boolean);
+  const detailsIdx = lines.findIndex((l) => l.startsWith("Gateway target: "));
+
+  const summaryLines = (detailsIdx >= 0 ? lines.slice(0, detailsIdx) : lines)
+    .map((l) => l.trim())
+    .filter(Boolean);
+  const detailLines = detailsIdx >= 0 ? lines.slice(detailsIdx) : [];
+
+  const summary = summaryLines.length > 0 ? summaryLines.join(" ") : message;
+  const header = colorize(rich, theme.error.bold, "Health check failed");
+
+  const out: string[] = [`${header}: ${summary}`];
+  for (const line of detailLines) {
+    out.push(`  ${formatKv(line, rich)}`);
+  }
+  return out.join("\n");
+}
diff --git a/src/daemon/launchd.ts b/src/daemon/launchd.ts
index 468af6f18..f20b9ca88 100644
--- a/src/daemon/launchd.ts
+++ b/src/daemon/launchd.ts
@@ -3,6 +3,7 @@ import fs from "node:fs/promises";
 import path from "node:path";
 import { promisify } from "node:util";
 
+import { colorize, isRich, theme } from "../terminal/theme.js";
 import {
   GATEWAY_LAUNCH_AGENT_LABEL,
   LEGACY_GATEWAY_LAUNCH_AGENT_LABELS,
@@ -11,6 +12,11 @@ import { parseKeyValueOutput } from "./runtime-parse.js";
 import type { GatewayServiceRuntime } from "./service-runtime.js";
 
 const execFileAsync = promisify(execFile);
+
+const formatLine = (label: string, value: string) => {
+  const rich = isRich();
+  return `${colorize(rich, theme.muted, `${label}:`)} ${colorize(rich, theme.command, value)}`;
+};
 function resolveHomeDir(env: Record<string, string | undefined>): string {
   const home = env.HOME?.trim() || env.USERPROFILE?.trim();
   if (!home) throw new Error("Missing HOME");
@@ -378,7 +384,9 @@ export async function uninstallLegacyLaunchAgents({
     const dest = path.join(trashDir, `${agent.label}.plist`);
     try {
       await fs.rename(agent.plistPath, dest);
-      stdout.write(`Moved legacy LaunchAgent to Trash: ${dest}\n`);
+      stdout.write(
+        `${formatLine("Moved legacy LaunchAgent to Trash", dest)}\n`,
+      );
     } catch {
       stdout.write(
         `Legacy LaunchAgent remains at ${agent.plistPath} (could not move)\n`,
@@ -414,7 +422,7 @@ export async function uninstallLaunchAgent({
   try {
     await fs.mkdir(trashDir, { recursive: true });
     await fs.rename(plistPath, dest);
-    stdout.write(`Moved LaunchAgent to Trash: ${dest}\n`);
+    stdout.write(`${formatLine("Moved LaunchAgent to Trash", dest)}\n`);
   } catch {
     stdout.write(`LaunchAgent remains at ${plistPath} (could not move)\n`);
   }
@@ -446,7 +454,7 @@ export async function stopLaunchAgent({
       `launchctl bootout failed: ${res.stderr || res.stdout}`.trim(),
     );
   }
-  stdout.write(`Stopped LaunchAgent: ${domain}/${label}\n`);
+  stdout.write(`${formatLine("Stopped LaunchAgent", `${domain}/${label}`)}\n`);
 }
 
 export async function installLaunchAgent({
@@ -507,8 +515,8 @@ export async function installLaunchAgent({
     `${domain}/${GATEWAY_LAUNCH_AGENT_LABEL}`,
   ]);
 
-  stdout.write(`Installed LaunchAgent: ${plistPath}\n`);
-  stdout.write(`Logs: ${stdoutPath}\n`);
+  stdout.write(`${formatLine("Installed LaunchAgent", plistPath)}\n`);
+  stdout.write(`${formatLine("Logs", stdoutPath)}\n`);
   return { plistPath };
 }
 
@@ -525,5 +533,7 @@ export async function restartLaunchAgent({
       `launchctl kickstart failed: ${res.stderr || res.stdout}`.trim(),
     );
   }
-  stdout.write(`Restarted LaunchAgent: ${domain}/${label}\n`);
+  stdout.write(
+    `${formatLine("Restarted LaunchAgent", `${domain}/${label}`)}\n`,
+  );
 }
diff --git a/src/daemon/schtasks.ts b/src/daemon/schtasks.ts
index c13d5ca32..565fed532 100644
--- a/src/daemon/schtasks.ts
+++ b/src/daemon/schtasks.ts
@@ -3,6 +3,7 @@ import fs from "node:fs/promises";
 import path from "node:path";
 import { promisify } from "node:util";
 
+import { colorize, isRich, theme } from "../terminal/theme.js";
 import {
   GATEWAY_WINDOWS_TASK_NAME,
   LEGACY_GATEWAY_WINDOWS_TASK_NAMES,
@@ -12,6 +13,11 @@ import type { GatewayServiceRuntime } from "./service-runtime.js";
 
 const execFileAsync = promisify(execFile);
 
+const formatLine = (label: string, value: string) => {
+  const rich = isRich();
+  return `${colorize(rich, theme.muted, `${label}:`)} ${colorize(rich, theme.command, value)}`;
+};
+
 function resolveHomeDir(env: Record<string, string | undefined>): string {
   const home = env.USERPROFILE?.trim() || env.HOME?.trim();
   if (!home) throw new Error("Missing HOME");
@@ -229,8 +235,10 @@ export async function installScheduledTask({
   }
 
   await execSchtasks(["/Run", "/TN", GATEWAY_WINDOWS_TASK_NAME]);
-  stdout.write(`Installed Scheduled Task: ${GATEWAY_WINDOWS_TASK_NAME}\n`);
-  stdout.write(`Task script: ${scriptPath}\n`);
+  stdout.write(
+    `${formatLine("Installed Scheduled Task", GATEWAY_WINDOWS_TASK_NAME)}\n`,
+  );
+  stdout.write(`${formatLine("Task script", scriptPath)}\n`);
   return { scriptPath };
 }
 
@@ -247,7 +255,7 @@ export async function uninstallScheduledTask({
   const scriptPath = resolveTaskScriptPath(env);
   try {
     await fs.unlink(scriptPath);
-    stdout.write(`Removed task script: ${scriptPath}\n`);
+    stdout.write(`${formatLine("Removed task script", scriptPath)}\n`);
   } catch {
     stdout.write(`Task script not found at ${scriptPath}\n`);
   }
@@ -272,7 +280,9 @@ export async function stopScheduledTask({
   if (res.code !== 0 && !isTaskNotRunning(res)) {
     throw new Error(`schtasks end failed: ${res.stderr || res.stdout}`.trim());
   }
-  stdout.write(`Stopped Scheduled Task: ${GATEWAY_WINDOWS_TASK_NAME}\n`);
+  stdout.write(
+    `${formatLine("Stopped Scheduled Task", GATEWAY_WINDOWS_TASK_NAME)}\n`,
+  );
 }
 
 export async function restartScheduledTask({
@@ -286,7 +296,9 @@ export async function restartScheduledTask({
   if (res.code !== 0) {
     throw new Error(`schtasks run failed: ${res.stderr || res.stdout}`.trim());
   }
-  stdout.write(`Restarted Scheduled Task: ${GATEWAY_WINDOWS_TASK_NAME}\n`);
+  stdout.write(
+    `${formatLine("Restarted Scheduled Task", GATEWAY_WINDOWS_TASK_NAME)}\n`,
+  );
 }
 
 export async function isScheduledTaskInstalled(): Promise<boolean> {
@@ -400,7 +412,9 @@ export async function uninstallLegacyScheduledTasks({
 
     try {
       await fs.unlink(task.scriptPath);
-      stdout.write(`Removed legacy task script: ${task.scriptPath}\n`);
+      stdout.write(
+        `${formatLine("Removed legacy task script", task.scriptPath)}\n`,
+      );
     } catch {
       stdout.write(`Legacy task script not found at ${task.scriptPath}\n`);
     }
diff --git a/src/daemon/systemd.ts b/src/daemon/systemd.ts
index 6d6496c8d..b39cd30cc 100644
--- a/src/daemon/systemd.ts
+++ b/src/daemon/systemd.ts
@@ -4,6 +4,7 @@ import os from "node:os";
 import path from "node:path";
 import { promisify } from "node:util";
 import { runCommandWithTimeout, runExec } from "../process/exec.js";
+import { colorize, isRich, theme } from "../terminal/theme.js";
 import {
   GATEWAY_SYSTEMD_SERVICE_NAME,
   LEGACY_GATEWAY_SYSTEMD_SERVICE_NAMES,
@@ -13,6 +14,11 @@ import type { GatewayServiceRuntime } from "./service-runtime.js";
 
 const execFileAsync = promisify(execFile);
 
+const formatLine = (label: string, value: string) => {
+  const rich = isRich();
+  return `${colorize(rich, theme.muted, `${label}:`)} ${colorize(rich, theme.command, value)}`;
+};
+
 function resolveHomeDir(env: Record<string, string | undefined>): string {
   const home = env.HOME?.trim() || env.USERPROFILE?.trim();
   if (!home) throw new Error("Missing HOME");
@@ -410,7 +416,7 @@ export async function installSystemdService({
     );
   }
 
-  stdout.write(`Installed systemd service: ${unitPath}\n`);
+  stdout.write(`${formatLine("Installed systemd service", unitPath)}\n`);
   return { unitPath };
 }
 
@@ -428,7 +434,7 @@ export async function uninstallSystemdService({
   const unitPath = resolveSystemdUnitPath(env);
   try {
     await fs.unlink(unitPath);
-    stdout.write(`Removed systemd service: ${unitPath}\n`);
+    stdout.write(`${formatLine("Removed systemd service", unitPath)}\n`);
   } catch {
     stdout.write(`Systemd service not found at ${unitPath}\n`);
   }
@@ -447,7 +453,7 @@ export async function stopSystemdService({
       `systemctl stop failed: ${res.stderr || res.stdout}`.trim(),
     );
   }
-  stdout.write(`Stopped systemd service: ${unitName}\n`);
+  stdout.write(`${formatLine("Stopped systemd service", unitName)}\n`);
 }
 
 export async function restartSystemdService({
@@ -463,7 +469,7 @@ export async function restartSystemdService({
       `systemctl restart failed: ${res.stderr || res.stdout}`.trim(),
     );
   }
-  stdout.write(`Restarted systemd service: ${unitName}\n`);
+  stdout.write(`${formatLine("Restarted systemd service", unitName)}\n`);
 }
 
 export async function isSystemdServiceEnabled(): Promise<boolean> {
@@ -584,7 +590,9 @@ export async function uninstallLegacySystemdUnits({
 
     try {
       await fs.unlink(unit.unitPath);
-      stdout.write(`Removed legacy systemd service: ${unit.unitPath}\n`);
+      stdout.write(
+        `${formatLine("Removed legacy systemd service", unit.unitPath)}\n`,
+      );
     } catch {
       stdout.write(`Legacy systemd unit not found at ${unit.unitPath}\n`);
     }
diff --git a/src/wizard/onboarding.ts b/src/wizard/onboarding.ts
index d67750f5f..302c9ec7e 100644
--- a/src/wizard/onboarding.ts
+++ b/src/wizard/onboarding.ts
@@ -13,6 +13,7 @@ import {
   type GatewayDaemonRuntime,
 } from "../commands/daemon-runtime.js";
 import { healthCommand } from "../commands/health.js";
+import { formatHealthCheckFailure } from "../commands/health-format.js";
 import {
   applyWizardMetadata,
   DEFAULT_WORKSPACE,
@@ -664,7 +665,7 @@ export async function runOnboardingWizard(
     try {
       await healthCommand({ json: false, timeoutMs: 10_000 }, runtime);
     } catch (err) {
-      runtime.error(`Health check failed: ${String(err)}`);
+      runtime.error(formatHealthCheckFailure(err));
       await prompter.note(
         [
           "Docs:",
@@ -740,7 +741,7 @@ export async function runOnboardingWizard(
         "Start TUI (best option!)",
       );
       const wantsTui = await prompter.confirm({
-        message: "Start TUI now? (best option!)",
+        message: "Do you want to hatch your bot now?",
         initialValue: true,
       });
       if (wantsTui) {