diff --git a/CHANGELOG.md b/CHANGELOG.md
index 68bc1f6f2..e3cc4a8e8 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -101,6 +101,7 @@
 - CLI: centralize lobster palette + apply it to onboarding/config prompts. — thanks @steipete
 - Gateway/CLI: add `clawdbot gateway --dev/--reset` to auto-create a dev config/workspace with a robot identity (no BOOTSTRAP.md), and reset wipes config/creds/sessions/workspace (subcommand --dev no longer collides with global --dev profile). — thanks @steipete
 - Configure: stop prompting to open the Control UI (still shown in onboarding). — thanks @steipete
+- Onboarding/TUI: prompt to start TUI (best option) when BOOTSTRAP.md exists and add `tui --message` to auto-send the first prompt. — thanks @steipete
 - Telegram: suppress grammY getUpdates stack traces; log concise retry message instead. — thanks @steipete
 - Gateway/CLI: allow dev profile (`clawdbot --dev`) to auto-create the dev config + workspace. — thanks @steipete
 - Dev templates: ship C-3PO dev workspace defaults as docs templates and use them for dev bootstrap. — thanks @steipete
diff --git a/docs/cli/index.md b/docs/cli/index.md
index d53131670..730ad9397 100644
--- a/docs/cli/index.md
+++ b/docs/cli/index.md
@@ -660,5 +660,6 @@ Options:
 - `--session <key>`
 - `--deliver`
 - `--thinking <level>`
+- `--message <text>`
 - `--timeout-ms <ms>`
 - `--history-limit <n>`
diff --git a/src/cli/tui-cli.ts b/src/cli/tui-cli.ts
index beb4f84f1..86ce7ca1d 100644
--- a/src/cli/tui-cli.ts
+++ b/src/cli/tui-cli.ts
@@ -18,6 +18,7 @@ export function registerTuiCli(program: Command) {
     )
     .option("--deliver", "Deliver assistant replies", false)
     .option("--thinking <level>", "Thinking level override")
+    .option("--message <text>", "Send an initial message after connecting")
     .option("--timeout-ms <ms>", "Agent timeout in ms", "30000")
     .option("--history-limit <n>", "History entries to load", "200")
     .action(async (opts) => {
@@ -37,6 +38,7 @@ export function registerTuiCli(program: Command) {
           session: opts.session as string | undefined,
           deliver: Boolean(opts.deliver),
           thinking: opts.thinking as string | undefined,
+          message: opts.message as string | undefined,
           timeoutMs: Number.isNaN(timeoutMs) ? undefined : timeoutMs,
           historyLimit: Number.isNaN(historyLimit) ? undefined : historyLimit,
         });
diff --git a/src/tui/tui.ts b/src/tui/tui.ts
index 204156beb..bda0d8bd5 100644
--- a/src/tui/tui.ts
+++ b/src/tui/tui.ts
@@ -34,6 +34,7 @@ export type TuiOptions = {
   thinking?: string;
   timeoutMs?: number;
   historyLimit?: number;
+  message?: string;
 };
 
 type ChatEvent = {
@@ -146,6 +147,8 @@ export async function runTui(opts: TuiOptions) {
   let toolsExpanded = false;
   let showThinking = false;
   let deliverDefault = Boolean(opts.deliver);
+  const autoMessage = opts.message?.trim();
+  let autoMessageSent = false;
   let sessionInfo: SessionInfo = {};
   let lastCtrlCAt = 0;
 
@@ -976,6 +979,10 @@ export async function runTui(opts: TuiOptions) {
         await loadHistory();
         chatLog.addSystem("gateway connected");
         tui.requestRender();
+        if (!autoMessageSent && autoMessage) {
+          autoMessageSent = true;
+          await sendMessage(autoMessage);
+        }
       } else {
         chatLog.addSystem("gateway reconnected");
       }
diff --git a/src/wizard/onboarding.ts b/src/wizard/onboarding.ts
index cb8459437..baaff9e58 100644
--- a/src/wizard/onboarding.ts
+++ b/src/wizard/onboarding.ts
@@ -1,5 +1,7 @@
+import fs from "node:fs/promises";
 import path from "node:path";
 import { ensureAuthProfileStore } from "../agents/auth-profiles.js";
+import { DEFAULT_BOOTSTRAP_FILENAME } from "../agents/workspace.js";
 import {
   applyAuthChoice,
   warnIfModelConfigLooksOff,
@@ -52,6 +54,7 @@ import { buildServiceEnvironment } from "../daemon/service-env.js";
 import { ensureControlUiAssetsBuilt } from "../infra/control-ui-assets.js";
 import type { RuntimeEnv } from "../runtime.js";
 import { defaultRuntime } from "../runtime.js";
+import { runTui } from "../tui/tui.js";
 import { resolveUserPath, sleep } from "../utils.js";
 import type { WizardPrompter } from "./prompts.js";
 
@@ -654,6 +657,11 @@ export async function runOnboardingWizard(
   const gatewayStatusLine = gatewayProbe.ok
     ? "Gateway: reachable"
     : `Gateway: not detected${gatewayProbe.detail ? ` (${gatewayProbe.detail})` : ""}`;
+  const bootstrapPath = path.join(workspaceDir, DEFAULT_BOOTSTRAP_FILENAME);
+  const hasBootstrap = await fs
+    .access(bootstrapPath)
+    .then(() => true)
+    .catch(() => false);
 
   await prompter.note(
     [
@@ -668,33 +676,58 @@ export async function runOnboardingWizard(
     "Control UI",
   );
 
-  const browserSupport = await detectBrowserOpenSupport();
   if (gatewayProbe.ok) {
-    if (!browserSupport.ok) {
+    if (hasBootstrap) {
       await prompter.note(
-        formatControlUiSshHint({
-          port,
-          basePath: baseConfig.gateway?.controlUi?.basePath,
-          token: authMode === "token" ? gatewayToken : undefined,
-        }),
-        "Open Control UI",
+        [
+          "This is the defining action that makes your agent you.",
+          "Please take your time.",
+          "The more you tell it, the better the experience will be.",
+          'We will send: "Wake up, my friend!"',
+        ].join("\n"),
+        "Start TUI (best option!)",
       );
-    } else {
-      const wantsOpen = await prompter.confirm({
-        message: "Open Control UI now?",
+      const wantsTui = await prompter.confirm({
+        message: "Start TUI now? (best option!)",
         initialValue: true,
       });
-      if (wantsOpen) {
-        const opened = await openUrl(`${links.httpUrl}${tokenParam}`);
-        if (!opened) {
-          await prompter.note(
-            formatControlUiSshHint({
-              port,
-              basePath: baseConfig.gateway?.controlUi?.basePath,
-              token: authMode === "token" ? gatewayToken : undefined,
-            }),
-            "Open Control UI",
-          );
+      if (wantsTui) {
+        await runTui({
+          url: links.wsUrl,
+          token: authMode === "token" ? gatewayToken : undefined,
+          password:
+            authMode === "password" ? baseConfig.gateway?.auth?.password : "",
+          message: "Wake up, my friend!",
+        });
+      }
+    } else {
+      const browserSupport = await detectBrowserOpenSupport();
+      if (!browserSupport.ok) {
+        await prompter.note(
+          formatControlUiSshHint({
+            port,
+            basePath: baseConfig.gateway?.controlUi?.basePath,
+            token: authMode === "token" ? gatewayToken : undefined,
+          }),
+          "Open Control UI",
+        );
+      } else {
+        const wantsOpen = await prompter.confirm({
+          message: "Open Control UI now?",
+          initialValue: true,
+        });
+        if (wantsOpen) {
+          const opened = await openUrl(`${links.httpUrl}${tokenParam}`);
+          if (!opened) {
+            await prompter.note(
+              formatControlUiSshHint({
+                port,
+                basePath: baseConfig.gateway?.controlUi?.basePath,
+                token: authMode === "token" ? gatewayToken : undefined,
+              }),
+              "Open Control UI",
+            );
+          }
         }
       }
     }