Merge branch 'main' into feat/plan-mode

Co-authored-by: Glucksberg <markuscontasul@gmail.com>

CHANGELOG.md

@@ -6,8 +6,10 @@ Docs: https://docs.clawd.bot
 Status: unreleased.
 
 ### Changes
-- Docs: add Fly private/hardened deployment guide. (#2121) Thanks @dguido.
+- Agents: honor tools.exec.safeBins in exec allowlist checks. (#2281)
+- Docs: tighten Fly private deployment steps. (#2289) Thanks @dguido.
 - Gateway: warn on hook tokens via query params; document header auth preference. (#2200) Thanks @YuriNachos.
+- Gateway: add dangerous Control UI device auth bypass flag + audit warnings. (#2248)
 - Doctor: warn on gateway exposure without auth. (#2016) Thanks @Alex-Alaniz.
 - Discord: add configurable privileged gateway intents for presences/members. (#2266) Thanks @kentaro.
 - Docs: add Vercel AI Gateway to providers sidebar. (#1901) Thanks @jerilynzheng.
@@ -18,9 +20,10 @@ Status: unreleased.
 - Docs: add DigitalOcean deployment guide. (#1870) Thanks @0xJonHoldsCrypto.
 - Docs: add Raspberry Pi install guide. (#1871) Thanks @0xJonHoldsCrypto.
 - Docs: add GCP Compute Engine deployment guide. (#1848) Thanks @hougangdev.
-- Docs: add LINE channel guide.
+- Docs: add LINE channel guide. Thanks @thewilloftheshadow.
 - Docs: credit both contributors for Control UI refresh. (#1852) Thanks @EnzeD.
 - Onboarding: add Venice API key to non-interactive flow. (#1893) Thanks @jonisjongithub.
+- Onboarding: strengthen security warning copy for beta + access control expectations.
 - Tlon: format thread reply IDs as @ud. (#1837) Thanks @wca4a.
 - Gateway: prefer newest session metadata when combining stores. (#1823) Thanks @emanuelst.
 - Web UI: keep sub-agent announce replies visible in WebChat. (#1977) Thanks @andrescardonas7.
@@ -29,6 +32,7 @@ Status: unreleased.
 - Browser: fall back to URL matching for extension relay target resolution. (#1999) Thanks @jonit-dev.
 - Update: ignore dist/control-ui for dirty checks and restore after ui builds. (#1976) Thanks @Glucksberg.
 - Telegram: allow caption param for media sends. (#1888) Thanks @mguellsegarra.
+- Telegram: support plugin sendPayload channelData (media/buttons) and validate plugin commands. (#1917) Thanks @JoshuaLelon.
 - Telegram: avoid block replies when streaming is disabled. (#1885) Thanks @ivancasco.
 - Auth: show copyable Google auth URL after ASCII prompt. (#1787) Thanks @robbyczgw-cla.
 - Routing: precompile session key regexes. (#1697) Thanks @Ray0907.
@@ -48,10 +52,12 @@ Status: unreleased.
 - Web UI: improve WebChat image paste previews and allow image-only sends. (#1925) Thanks @smartprogrammer93.
 - Security: wrap external hook content by default with a per-hook opt-out. (#1827) Thanks @mertcicekci0.
 - Gateway: default auth now fail-closed (token/password required; Tailscale Serve identity remains allowed).
+- Onboarding: remove unsupported gateway auth "off" choice from onboarding/configure flows and CLI flags.
 
 ## 2026.1.24-3
 
 ### Fixes
+- Slack: fix image downloads failing due to missing Authorization header on cross-origin redirects. (#1936) Thanks @sanderhelgesen.
 - Gateway: harden reverse proxy handling for local-client detection and unauthenticated proxied connects. (#1795) Thanks @orlyjamie.
 - Security audit: flag loopback Control UI with auth disabled as critical. (#1795) Thanks @orlyjamie.
 - CLI: resume claude-cli sessions and stream CLI replies to TUI clients. (#1921) Thanks @rmorse.

README.md

@@ -479,32 +479,33 @@ Thanks to all clawtributors:
 <p align="left">
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+  <a href="https://github.com/juanpablodlc"><img src="https://avatars.githubusercontent.com/u/92012363?v=4&s=48" width="48" height="48" alt="juanpablodlc" title="juanpablodlc"/></a> <a href="https://github.com/hsrvc"><img src="https://avatars.githubusercontent.com/u/129702169?v=4&s=48" width="48" height="48" alt="hsrvc" title="hsrvc"/></a> <a href="https://github.com/magimetal"><img src="https://avatars.githubusercontent.com/u/36491250?v=4&s=48" width="48" height="48" alt="magimetal" title="magimetal"/></a> <a href="https://github.com/zerone0x"><img src="https://avatars.githubusercontent.com/u/39543393?v=4&s=48" width="48" height="48" alt="zerone0x" title="zerone0x"/></a> <a href="https://github.com/meaningfool"><img src="https://avatars.githubusercontent.com/u/2862331?v=4&s=48" width="48" height="48" alt="meaningfool" title="meaningfool"/></a> <a href="https://github.com/tyler6204"><img src="https://avatars.githubusercontent.com/u/64381258?v=4&s=48" width="48" height="48" alt="tyler6204" title="tyler6204"/></a> <a href="https://github.com/patelhiren"><img src="https://avatars.githubusercontent.com/u/172098?v=4&s=48" width="48" height="48" alt="patelhiren" title="patelhiren"/></a> <a href="https://github.com/NicholasSpisak"><img src="https://avatars.githubusercontent.com/u/129075147?v=4&s=48" width="48" height="48" alt="NicholasSpisak" title="NicholasSpisak"/></a> <a href="https://github.com/jonisjongithub"><img src="https://avatars.githubusercontent.com/u/86072337?v=4&s=48" width="48" height="48" alt="jonisjongithub" title="jonisjongithub"/></a> <a href="https://github.com/AbhisekBasu1"><img src="https://avatars.githubusercontent.com/u/40645221?v=4&s=48" width="48" height="48" alt="abhisekbasu1" title="abhisekbasu1"/></a>
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+  <a href="https://github.com/search?q=Jefferson%20Nunn"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Jefferson Nunn" title="Jefferson Nunn"/></a> <a href="https://github.com/search?q=Kevin%20Lin"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Kevin Lin" title="Kevin Lin"/></a> <a href="https://github.com/kitze"><img src="https://avatars.githubusercontent.com/u/1160594?v=4&s=48" width="48" height="48" alt="kitze" title="kitze"/></a> <a href="https://github.com/levifig"><img src="https://avatars.githubusercontent.com/u/1605?v=4&s=48" width="48" height="48" alt="levifig" title="levifig"/></a> <a href="https://github.com/search?q=Lloyd"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Lloyd" title="Lloyd"/></a> <a href="https://github.com/loukotal"><img src="https://avatars.githubusercontent.com/u/18210858?v=4&s=48" width="48" height="48" alt="loukotal" title="loukotal"/></a> <a href="https://github.com/louzhixian"><img src="https://avatars.githubusercontent.com/u/7994361?v=4&s=48" width="48" height="48" alt="louzhixian" title="louzhixian"/></a> <a href="https://github.com/martinpucik"><img src="https://avatars.githubusercontent.com/u/5503097?v=4&s=48" width="48" height="48" alt="martinpucik" title="martinpucik"/></a> <a href="https://github.com/search?q=Matt%20mini"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Matt mini" title="Matt mini"/></a> <a href="https://github.com/mertcicekci0"><img src="https://avatars.githubusercontent.com/u/179321902?v=4&s=48" width="48" height="48" alt="mertcicekci0" title="mertcicekci0"/></a>
+  <a href="https://github.com/search?q=Miles"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Miles" title="Miles"/></a> <a href="https://github.com/mrdbstn"><img src="https://avatars.githubusercontent.com/u/58957632?v=4&s=48" width="48" height="48" alt="mrdbstn" title="mrdbstn"/></a> <a href="https://github.com/MSch"><img src="https://avatars.githubusercontent.com/u/7475?v=4&s=48" width="48" height="48" alt="MSch" title="MSch"/></a> <a href="https://github.com/search?q=Mustafa%20Tag%20Eldeen"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Mustafa Tag Eldeen" title="Mustafa Tag Eldeen"/></a> <a href="https://github.com/ndraiman"><img src="https://avatars.githubusercontent.com/u/12609607?v=4&s=48" width="48" height="48" alt="ndraiman" title="ndraiman"/></a> <a href="https://github.com/nexty5870"><img src="https://avatars.githubusercontent.com/u/3869659?v=4&s=48" width="48" height="48" alt="nexty5870" title="nexty5870"/></a> <a href="https://github.com/Noctivoro"><img src="https://avatars.githubusercontent.com/u/183974570?v=4&s=48" width="48" height="48" alt="Noctivoro" title="Noctivoro"/></a> <a href="https://github.com/prathamdby"><img src="https://avatars.githubusercontent.com/u/134331217?v=4&s=48" width="48" height="48" alt="prathamdby" title="prathamdby"/></a> <a href="https://github.com/ptn1411"><img src="https://avatars.githubusercontent.com/u/57529765?v=4&s=48" width="48" height="48" alt="ptn1411" title="ptn1411"/></a> <a href="https://github.com/reeltimeapps"><img src="https://avatars.githubusercontent.com/u/637338?v=4&s=48" width="48" height="48" alt="reeltimeapps" title="reeltimeapps"/></a>
+  <a href="https://github.com/RLTCmpe"><img src="https://avatars.githubusercontent.com/u/10762242?v=4&s=48" width="48" height="48" alt="RLTCmpe" title="RLTCmpe"/></a> <a href="https://github.com/search?q=Rolf%20Fredheim"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Rolf Fredheim" title="Rolf Fredheim"/></a> <a href="https://github.com/search?q=Rony%20Kelner"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Rony Kelner" title="Rony Kelner"/></a> <a href="https://github.com/search?q=Samrat%20Jha"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Samrat Jha" title="Samrat Jha"/></a> <a href="https://github.com/senoldogann"><img src="https://avatars.githubusercontent.com/u/45736551?v=4&s=48" width="48" height="48" alt="senoldogann" title="senoldogann"/></a> <a href="https://github.com/Seredeep"><img src="https://avatars.githubusercontent.com/u/22802816?v=4&s=48" width="48" height="48" alt="Seredeep" title="Seredeep"/></a> <a href="https://github.com/sergical"><img src="https://avatars.githubusercontent.com/u/3760543?v=4&s=48" width="48" height="48" alt="sergical" title="sergical"/></a> <a href="https://github.com/shiv19"><img src="https://avatars.githubusercontent.com/u/9407019?v=4&s=48" width="48" height="48" alt="shiv19" title="shiv19"/></a> <a href="https://github.com/shiyuanhai"><img src="https://avatars.githubusercontent.com/u/1187370?v=4&s=48" width="48" height="48" alt="shiyuanhai" title="shiyuanhai"/></a> <a href="https://github.com/siraht"><img src="https://avatars.githubusercontent.com/u/73152895?v=4&s=48" width="48" height="48" alt="siraht" title="siraht"/></a>
+  <a href="https://github.com/snopoke"><img src="https://avatars.githubusercontent.com/u/249606?v=4&s=48" width="48" height="48" alt="snopoke" title="snopoke"/></a> <a href="https://github.com/testingabc321"><img src="https://avatars.githubusercontent.com/u/8577388?v=4&s=48" width="48" height="48" alt="testingabc321" title="testingabc321"/></a> <a href="https://github.com/search?q=The%20Admiral"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="The Admiral" title="The Admiral"/></a> <a href="https://github.com/thesash"><img src="https://avatars.githubusercontent.com/u/1166151?v=4&s=48" width="48" height="48" alt="thesash" title="thesash"/></a> <a href="https://github.com/search?q=Ubuntu"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Ubuntu" title="Ubuntu"/></a> <a href="https://github.com/voidserf"><img src="https://avatars.githubusercontent.com/u/477673?v=4&s=48" width="48" height="48" alt="voidserf" title="voidserf"/></a> <a href="https://github.com/search?q=Vultr-Clawd%20Admin"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Vultr-Clawd Admin" title="Vultr-Clawd Admin"/></a> <a href="https://github.com/search?q=Wimmie"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Wimmie" title="Wimmie"/></a> <a href="https://github.com/wstock"><img src="https://avatars.githubusercontent.com/u/1394687?v=4&s=48" width="48" height="48" alt="wstock" title="wstock"/></a> <a href="https://github.com/yazinsai"><img src="https://avatars.githubusercontent.com/u/1846034?v=4&s=48" width="48" height="48" alt="yazinsai" title="yazinsai"/></a>
+  <a href="https://github.com/search?q=ymat19"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="ymat19" title="ymat19"/></a> <a href="https://github.com/search?q=Zach%20Knickerbocker"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Zach Knickerbocker" title="Zach Knickerbocker"/></a> <a href="https://github.com/0xJonHoldsCrypto"><img src="https://avatars.githubusercontent.com/u/81202085?v=4&s=48" width="48" height="48" alt="0xJonHoldsCrypto" title="0xJonHoldsCrypto"/></a> <a href="https://github.com/aaronn"><img src="https://avatars.githubusercontent.com/u/1653630?v=4&s=48" width="48" height="48" alt="aaronn" title="aaronn"/></a> <a href="https://github.com/Alphonse-arianee"><img src="https://avatars.githubusercontent.com/u/254457365?v=4&s=48" width="48" height="48" alt="Alphonse-arianee" title="Alphonse-arianee"/></a> <a href="https://github.com/atalovesyou"><img src="https://avatars.githubusercontent.com/u/3534502?v=4&s=48" width="48" height="48" alt="atalovesyou" title="atalovesyou"/></a> <a href="https://github.com/search?q=Azade"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Azade" title="Azade"/></a> <a href="https://github.com/carlulsoe"><img src="https://avatars.githubusercontent.com/u/34673973?v=4&s=48" width="48" height="48" alt="carlulsoe" title="carlulsoe"/></a> <a href="https://github.com/search?q=ddyo"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="ddyo" title="ddyo"/></a> <a href="https://github.com/search?q=Erik"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Erik" title="Erik"/></a>
+  <a href="https://github.com/hougangdev"><img src="https://avatars.githubusercontent.com/u/105773686?v=4&s=48" width="48" height="48" alt="hougangdev" title="hougangdev"/></a> <a href="https://github.com/latitudeki5223"><img src="https://avatars.githubusercontent.com/u/119656367?v=4&s=48" width="48" height="48" alt="latitudeki5223" title="latitudeki5223"/></a> <a href="https://github.com/search?q=Manuel%20Maly"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Manuel Maly" title="Manuel Maly"/></a> <a href="https://github.com/search?q=Mourad%20Boustani"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Mourad Boustani" title="Mourad Boustani"/></a> <a href="https://github.com/odrobnik"><img src="https://avatars.githubusercontent.com/u/333270?v=4&s=48" width="48" height="48" alt="odrobnik" title="odrobnik"/></a> <a href="https://github.com/pcty-nextgen-ios-builder"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="pcty-nextgen-ios-builder" title="pcty-nextgen-ios-builder"/></a> <a href="https://github.com/search?q=Quentin"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Quentin" title="Quentin"/></a> <a href="https://github.com/search?q=Randy%20Torres"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Randy Torres" title="Randy Torres"/></a> <a href="https://github.com/rhjoh"><img src="https://avatars.githubusercontent.com/u/105699450?v=4&s=48" width="48" height="48" alt="rhjoh" title="rhjoh"/></a> <a href="https://github.com/ronak-guliani"><img src="https://avatars.githubusercontent.com/u/23518228?v=4&s=48" width="48" height="48" alt="ronak-guliani" title="ronak-guliani"/></a>
+  <a href="https://github.com/search?q=William%20Stock"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="William Stock" title="William Stock"/></a>
 </p>

docs/cli/index.md

@@ -314,7 +314,7 @@ Options:
 - `--opencode-zen-api-key <key>`
 - `--gateway-port <port>`
 - `--gateway-bind <loopback|lan|tailnet|auto|custom>`
-- `--gateway-auth <off|token|password>`
+- `--gateway-auth <token|password>`
 - `--gateway-token <token>`
 - `--gateway-password <password>`
 - `--remote-url <url>`

docs/gateway/configuration.md

@@ -2847,9 +2847,11 @@ Control UI base path:
 - `gateway.controlUi.basePath` sets the URL prefix where the Control UI is served.
 - Examples: `"/ui"`, `"/clawdbot"`, `"/apps/clawdbot"`.
 - Default: root (`/`) (unchanged).
-- `gateway.controlUi.allowInsecureAuth` allows token-only auth for the Control UI and skips
-  device identity + pairing (even on HTTPS). Default: `false`. Prefer HTTPS
+- `gateway.controlUi.allowInsecureAuth` allows token-only auth for the Control UI when
+  device identity is omitted (typically over HTTP). Default: `false`. Prefer HTTPS
   (Tailscale Serve) or `127.0.0.1`.
+- `gateway.controlUi.dangerouslyDisableDeviceAuth` disables device identity checks for the
+  Control UI (token/password only). Default: `false`. Break-glass only.
 
 Related docs:
 - [Control UI](/web/control-ui)

docs/gateway/protocol.md

@@ -198,7 +198,8 @@ The Gateway treats these as **claims** and enforces server-side allowlists.
 - **Local** connects include loopback and the gateway host’s own tailnet address
   (so same‑host tailnet binds can still auto‑approve).
 - All WS clients must include `device` identity during `connect` (operator + node).
-  Control UI can omit it **only** when `gateway.controlUi.allowInsecureAuth` is enabled.
+  Control UI can omit it **only** when `gateway.controlUi.allowInsecureAuth` is enabled
+  (or `gateway.controlUi.dangerouslyDisableDeviceAuth` for break-glass use).
 - Non-local connections must sign the server-provided `connect.challenge` nonce.
 
 ## TLS + pinning

docs/gateway/security.md

@@ -58,9 +58,13 @@ When the audit prints findings, treat this as a priority order:
 
 The Control UI needs a **secure context** (HTTPS or localhost) to generate device
 identity. If you enable `gateway.controlUi.allowInsecureAuth`, the UI falls back
-to **token-only auth** and skips device pairing (even on HTTPS). This is a security
+to **token-only auth** and skips device pairing when device identity is omitted. This is a security
 downgrade—prefer HTTPS (Tailscale Serve) or open the UI on `127.0.0.1`.
 
+For break-glass scenarios only, `gateway.controlUi.dangerouslyDisableDeviceAuth`
+disables device identity checks entirely. This is a severe security downgrade;
+keep it off unless you are actively debugging and can revert quickly.
+
 `clawdbot security audit` warns when this setting is enabled.
 
 ## Reverse Proxy Configuration

docs/gateway/troubleshooting.md

@@ -214,7 +214,7 @@ the Gateway likely refused to bind.
 - Fix: run `clawdbot doctor` to update it (or `clawdbot gateway install --force` for a full rewrite).
 
 **If `Last gateway error:` mentions “refusing to bind … without auth”**
-- You set `gateway.bind` to a non-loopback mode (`lan`/`tailnet`/`custom`, or `auto` when loopback is unavailable) but left auth off.
+- You set `gateway.bind` to a non-loopback mode (`lan`/`tailnet`/`custom`, or `auto` when loopback is unavailable) but didn’t configure auth.
 - Fix: set `gateway.auth.mode` + `gateway.auth.token` (or export `CLAWDBOT_GATEWAY_TOKEN`) and restart the service.
 
 **If `clawdbot gateway status` says `bind=tailnet` but no tailnet interface was found**

src/agents/pi-tools.safe-bins.test.ts

@@ -0,0 +1,78 @@
+import fs from "node:fs";
+import os from "node:os";
+import path from "node:path";
+import { describe, expect, it, vi } from "vitest";
+import type { ClawdbotConfig } from "../config/config.js";
+import type { ExecApprovalsResolved } from "../infra/exec-approvals.js";
+import { createClawdbotCodingTools } from "./pi-tools.js";
+
+vi.mock("../infra/exec-approvals.js", async (importOriginal) => {
+  const mod = await importOriginal<typeof import("../infra/exec-approvals.js")>();
+  const approvals: ExecApprovalsResolved = {
+    path: "/tmp/exec-approvals.json",
+    socketPath: "/tmp/exec-approvals.sock",
+    token: "token",
+    defaults: {
+      security: "allowlist",
+      ask: "off",
+      askFallback: "deny",
+      autoAllowSkills: false,
+    },
+    agent: {
+      security: "allowlist",
+      ask: "off",
+      askFallback: "deny",
+      autoAllowSkills: false,
+    },
+    allowlist: [],
+    file: {
+      version: 1,
+      socket: { path: "/tmp/exec-approvals.sock", token: "token" },
+      defaults: {
+        security: "allowlist",
+        ask: "off",
+        askFallback: "deny",
+        autoAllowSkills: false,
+      },
+      agents: {},
+    },
+  };
+  return { ...mod, resolveExecApprovals: () => approvals };
+});
+
+describe("createClawdbotCodingTools safeBins", () => {
+  it("threads tools.exec.safeBins into exec allowlist checks", async () => {
+    if (process.platform === "win32") return;
+
+    const tmpDir = fs.mkdtempSync(path.join(os.tmpdir(), "clawdbot-safe-bins-"));
+    const cfg: ClawdbotConfig = {
+      tools: {
+        exec: {
+          host: "gateway",
+          security: "allowlist",
+          ask: "off",
+          safeBins: ["echo"],
+        },
+      },
+    };
+
+    const tools = createClawdbotCodingTools({
+      config: cfg,
+      sessionKey: "agent:main:main",
+      workspaceDir: tmpDir,
+      agentDir: path.join(tmpDir, "agent"),
+    });
+    const execTool = tools.find((tool) => tool.name === "exec");
+    expect(execTool).toBeDefined();
+
+    const marker = `safe-bins-${Date.now()}`;
+    const result = await execTool!.execute("call1", {
+      command: `echo ${marker}`,
+      workdir: tmpDir,
+    });
+    const text = result.content.find((content) => content.type === "text")?.text ?? "";
+
+    expect(result.details.status).toBe("completed");
+    expect(text).toContain(marker);
+  });
+});

src/agents/pi-tools.ts

@@ -86,6 +86,7 @@ function resolveExecConfig(cfg: ClawdbotConfig | undefined) {
     ask: globalExec?.ask,
     node: globalExec?.node,
     pathPrepend: globalExec?.pathPrepend,
+    safeBins: globalExec?.safeBins,
     backgroundMs: globalExec?.backgroundMs,
     timeoutSec: globalExec?.timeoutSec,
     approvalRunningNoticeMs: globalExec?.approvalRunningNoticeMs,
@@ -235,6 +236,7 @@ export function createClawdbotCodingTools(options?: {
     ask: options?.exec?.ask ?? execConfig.ask,
     node: options?.exec?.node ?? execConfig.node,
     pathPrepend: options?.exec?.pathPrepend ?? execConfig.pathPrepend,
+    safeBins: options?.exec?.safeBins ?? execConfig.safeBins,
     agentId,
     cwd: options?.workspaceDir,
     allowBackground,

src/agents/system-prompt.test.ts

@@ -310,6 +310,16 @@ describe("buildAgentSystemPrompt", () => {
     expect(prompt).toContain("/status shows Reasoning");
   });
 
+  it("includes /plan mode instructions", () => {
+    const prompt = buildAgentSystemPrompt({
+      workspaceDir: "/tmp/clawd",
+    });
+
+    expect(prompt).toContain("## Plan Mode (/plan)");
+    expect(prompt).toContain("If the user message starts with /plan");
+    expect(prompt).toContain("plans/<timestamp>-<slug>/");
+  });
+
   it("builds runtime line with agent and channel details", () => {
     const line = buildRuntimeLine(
       {

src/agents/system-prompt.ts

@@ -558,6 +558,27 @@ export function buildAgentSystemPrompt(params: {
     );
   }
 
+  // Plan mode is conversational but stateful: compile a messy goal into a structured artifact.
+  if (!isMinimal) {
+    lines.push(
+      "## Plan Mode (/plan)",
+      "If the user message starts with /plan, enter *planning mode*.",
+      "- Treat everything after /plan as the goal.",
+      "- Ask targeted follow-up questions (one at a time) to remove ambiguity.",
+      "- Persist state in the workspace so planning can resume without losing context.",
+      "",
+      "Artifacts:",
+      "- Create a directory plans/<timestamp>-<slug>/ in the workspace.",
+      "- Maintain plans/<id>/answers.json (incremental) and plans/<id>/plan.md (human-readable).",
+      "- Optionally create plans/<id>/plan.json (structured) when helpful.",
+      "",
+      "Rules:",
+      "- Be token-efficient: do not restate the entire plan on every turn; ask the next question.",
+      "- When enough information is collected, produce a crisp plan with milestones + next actions.",
+      "",
+    );
+  }
+
   lines.push(
     "## Runtime",
     buildRuntimeLine(runtimeInfo, runtimeChannel, runtimeCapabilities, params.defaultThinkLevel),

src/auto-reply/commands-registry.data.ts

@@ -157,6 +157,20 @@ function buildChatCommands(): ChatCommandDefinition[] {
       description: "Show current status.",
       textAlias: "/status",
     }),
+    defineChatCommand({
+      key: "plan",
+      nativeName: "plan",
+      description: "Interactive project planning (/plan) with saved artifacts.",
+      textAlias: "/plan",
+      acceptsArgs: true,
+    }),
+    defineChatCommand({
+      key: "plans",
+      nativeName: "plans",
+      description: "List/show/rename saved /plan artifacts.",
+      textAlias: "/plans",
+      acceptsArgs: true,
+    }),
     defineChatCommand({
       key: "allowlist",
       description: "List/add/remove allowlist entries.",

src/auto-reply/reply/commands-core.ts

@@ -27,6 +27,8 @@ import {
   handleUsageCommand,
 } from "./commands-session.js";
 import { handlePluginCommand } from "./commands-plugin.js";
+import { handlePlansCommand } from "./commands-plans.js";
+import { handlePlanCommand } from "./commands-plan.js";
 import type {
   CommandHandler,
   CommandHandlerResult,
@@ -43,6 +45,8 @@ const HANDLERS: CommandHandler[] = [
   handleRestartCommand,
   handleTtsCommands,
   handleHelpCommand,
+  handlePlanCommand,
+  handlePlansCommand,
   handleCommandsListCommand,
   handleStatusCommand,
   handleAllowlistCommand,

src/auto-reply/reply/commands-plan.test.ts

@@ -0,0 +1,396 @@
+import fs from "node:fs/promises";
+import os from "node:os";
+import path from "node:path";
+
+import { afterAll, beforeAll, beforeEach, describe, expect, it, vi } from "vitest";
+
+import type { ClawdbotConfig } from "../../config/config.js";
+import type { MsgContext } from "../templating.js";
+import { buildCommandContext, handleCommands } from "./commands.js";
+import { parseInlineDirectives } from "./directive-handling.js";
+
+const CANCEL = Symbol.for("clack:cancel");
+
+const hoisted = vi.hoisted(() => {
+  const state = {
+    selectQueue: [] as any[],
+    textQueue: [] as any[],
+    confirmQueue: [] as any[],
+    multiselectQueue: [] as any[],
+
+    // Embedded runner control
+    baseQuestions: [
+      {
+        id: "budget",
+        section: "Constraints",
+        prompt: "Budget?",
+        kind: "select",
+        required: true,
+        options: ["$", "$$"],
+      },
+      {
+        id: "deadline",
+        section: "Timeline",
+        prompt: "Deadline?",
+        kind: "text",
+      },
+    ] as any[],
+    extraQuestions: [
+      {
+        id: "transport",
+        section: "Constraints",
+        prompt: "Preferred transport?",
+        kind: "multiselect",
+        required: true,
+        options: ["Car", "Plane"],
+      },
+    ] as any[],
+  };
+
+  function resetQueues() {
+    state.selectQueue = [];
+    state.textQueue = [];
+    state.confirmQueue = [];
+    state.multiselectQueue = [];
+  }
+
+  const clack = {
+    select: vi.fn(async ({ options, message }: any) => {
+      const queued = state.selectQueue.shift();
+      if (queued !== undefined) return queued;
+
+      // Default behavior: choose first section once, then review.
+      if (String(message).includes("Choose a section")) {
+        // If we already chose a section once, go to review.
+        const already = (clack.select as any)._chosenOnce === true;
+        (clack.select as any)._chosenOnce = true;
+        if (already) return "__review";
+        return options[0].value;
+      }
+
+      return options[0].value;
+    }),
+    text: vi.fn(async ({ initialValue }: any) => {
+      const queued = state.textQueue.shift();
+      if (queued !== undefined) return queued;
+      return initialValue ?? "";
+    }),
+    confirm: vi.fn(async () => {
+      const queued = state.confirmQueue.shift();
+      if (queued !== undefined) return queued;
+      return true;
+    }),
+    multiselect: vi.fn(async ({ options }: any) => {
+      const queued = state.multiselectQueue.shift();
+      if (queued !== undefined) return queued;
+      return options.map((o: any) => o.value);
+    }),
+    isCancel: vi.fn((v: any) => v === CANCEL),
+  };
+
+  const embedded = {
+    runEmbeddedPiAgent: vi.fn(async ({ prompt }: any) => {
+      if (String(prompt).includes("Generate a compact questionnaire")) {
+        return {
+          payloads: [
+            {
+              text: JSON.stringify({
+                goal: "demo",
+                questions: state.baseQuestions,
+              }),
+            },
+          ],
+        };
+      }
+
+      if (String(prompt).includes("propose any missing high-signal questions")) {
+        return {
+          payloads: [
+            {
+              text: JSON.stringify({
+                goal: "demo",
+                questions: state.extraQuestions,
+              }),
+            },
+          ],
+        };
+      }
+
+      return {
+        payloads: [{ text: JSON.stringify({ ok: true }) }],
+      };
+    }),
+  };
+
+  return { state, resetQueues, clack, embedded };
+});
+
+// Mock clack prompts to simulate TUI interaction.
+vi.mock("@clack/prompts", async () => {
+  return {
+    confirm: hoisted.clack.confirm,
+    isCancel: hoisted.clack.isCancel,
+    select: hoisted.clack.select,
+    multiselect: hoisted.clack.multiselect,
+    text: hoisted.clack.text,
+  };
+});
+
+// llm-task extension dynamically imports embedded runner in src-first/dist-fallback form.
+vi.mock("../../../src/agents/pi-embedded-runner.js", () => ({
+  runEmbeddedPiAgent: hoisted.embedded.runEmbeddedPiAgent,
+}));
+vi.mock("../../../agents/pi-embedded-runner.js", () => ({
+  runEmbeddedPiAgent: hoisted.embedded.runEmbeddedPiAgent,
+}));
+
+let testWorkspaceDir = os.tmpdir();
+
+beforeAll(async () => {
+  testWorkspaceDir = await fs.mkdtemp(path.join(os.tmpdir(), "clawdbot-plan-"));
+  await fs.writeFile(path.join(testWorkspaceDir, "AGENTS.md"), "# Agents\n", "utf-8");
+});
+
+afterAll(async () => {
+  await fs.rm(testWorkspaceDir, { recursive: true, force: true });
+});
+
+beforeEach(() => {
+  hoisted.resetQueues();
+  (hoisted.clack.select as any)._chosenOnce = false;
+  // defaults
+  hoisted.state.baseQuestions = [
+    {
+      id: "budget",
+      section: "Constraints",
+      prompt: "Budget?",
+      kind: "select",
+      required: true,
+      options: ["$", "$$"],
+    },
+    {
+      id: "deadline",
+      section: "Timeline",
+      prompt: "Deadline?",
+      kind: "text",
+    },
+  ];
+  hoisted.state.extraQuestions = [
+    {
+      id: "transport",
+      section: "Constraints",
+      prompt: "Preferred transport?",
+      kind: "multiselect",
+      required: true,
+      options: ["Car", "Plane"],
+    },
+  ];
+});
+
+function buildParams(commandBody: string, cfg: ClawdbotConfig, ctxOverrides?: Partial<MsgContext>) {
+  const ctx = {
+    Body: commandBody,
+    CommandBody: commandBody,
+    CommandSource: "cli",
+    CommandAuthorized: true,
+    Provider: "cli",
+    Surface: "cli",
+    ...ctxOverrides,
+  } as MsgContext;
+
+  const command = buildCommandContext({
+    ctx,
+    cfg,
+    isGroup: false,
+    triggerBodyNormalized: commandBody.trim().toLowerCase(),
+    commandAuthorized: true,
+  });
+
+  return {
+    ctx,
+    cfg,
+    command,
+    directives: parseInlineDirectives(commandBody),
+    elevated: { enabled: true, allowed: true, failures: [] },
+    sessionKey: "agent:main:main",
+    workspaceDir: testWorkspaceDir,
+    defaultGroupActivation: () => "mention",
+    resolvedVerboseLevel: "off" as const,
+    resolvedReasoningLevel: "off" as const,
+    resolveDefaultThinkingLevel: async () => undefined,
+    provider: "cli",
+    model: "test-model",
+    contextTokens: 0,
+    isGroup: false,
+  };
+}
+
+async function getLatestPlanDir() {
+  const plansDir = path.join(testWorkspaceDir, "plans");
+  const entries = await fs.readdir(plansDir, { withFileTypes: true });
+  const dirs = entries.filter((e) => e.isDirectory()).map((e) => e.name);
+  expect(dirs.length).toBeGreaterThan(0);
+  // Sort for determinism (timestamp prefix in name)
+  dirs.sort();
+  return path.join(plansDir, dirs[dirs.length - 1]);
+}
+
+describe("/plan TUI", () => {
+  it("creates a plan directory and writes plan.md + answers.json + questions.json", async () => {
+    (process.stdin as any).isTTY = true;
+    (process.stdout as any).isTTY = true;
+
+    const cfg = {
+      commands: { text: true },
+      agents: { defaults: { model: { primary: "openai/mock-1" } } },
+    } as ClawdbotConfig;
+
+    const result = await handleCommands(buildParams("/plan plan a trip", cfg));
+
+    expect(result.shouldContinue).toBe(false);
+    expect(result.reply?.text).toContain("Plan saved");
+
+    const createdDir = await getLatestPlanDir();
+
+    const planMd = await fs.readFile(path.join(createdDir, "plan.md"), "utf-8");
+    const answers = JSON.parse(await fs.readFile(path.join(createdDir, "answers.json"), "utf-8"));
+    const questions = JSON.parse(
+      await fs.readFile(path.join(createdDir, "questions.json"), "utf-8"),
+    );
+
+    expect(planMd).toContain("# Plan");
+    expect(Object.keys(answers).length).toBeGreaterThan(0);
+    expect(questions.questions.length).toBeGreaterThan(0);
+  });
+
+  it("supports one-time extension at the end and uses multiselect for extra questions", async () => {
+    (process.stdin as any).isTTY = true;
+    (process.stdout as any).isTTY = true;
+
+    // Ensure we accept the extra questions and multiselect returns both.
+    hoisted.state.confirmQueue.push(true);
+    hoisted.state.multiselectQueue.push(["Car", "Plane"]);
+
+    const cfg = {
+      commands: { text: true },
+      agents: { defaults: { model: { primary: "openai/mock-1" } } },
+    } as ClawdbotConfig;
+
+    const result = await handleCommands(buildParams("/plan plan a trip", cfg));
+    expect(result.shouldContinue).toBe(false);
+
+    const createdDir = await getLatestPlanDir();
+    const answers = JSON.parse(await fs.readFile(path.join(createdDir, "answers.json"), "utf-8"));
+    const questions = JSON.parse(
+      await fs.readFile(path.join(createdDir, "questions.json"), "utf-8"),
+    );
+
+    expect(questions.questions.some((q: any) => q.id === "transport")).toBe(true);
+    expect(Array.isArray(answers.transport)).toBe(true);
+    expect(answers.transport).toEqual(["Car", "Plane"]);
+    expect(hoisted.clack.multiselect).toHaveBeenCalled();
+  });
+
+  it("does not ask extension confirm when extension returns no extra questions", async () => {
+    (process.stdin as any).isTTY = true;
+    (process.stdout as any).isTTY = true;
+
+    hoisted.state.extraQuestions = [];
+
+    const cfg = {
+      commands: { text: true },
+      agents: { defaults: { model: { primary: "openai/mock-1" } } },
+    } as ClawdbotConfig;
+
+    const result = await handleCommands(buildParams("/plan plan a trip", cfg));
+    expect(result.shouldContinue).toBe(false);
+
+    // confirm might still be used for other prompts; but in this template it shouldn't.
+    // We assert it was not called with the extension message.
+    const confirmCalls = (hoisted.clack.confirm as any).mock.calls as any[];
+    const extensionCall = confirmCalls.find((c) =>
+      String(c?.[0]?.message ?? "").includes("tighter the plan"),
+    );
+    expect(extensionCall).toBeUndefined();
+  });
+
+  it("dedupes extension questions by id", async () => {
+    (process.stdin as any).isTTY = true;
+    (process.stdout as any).isTTY = true;
+
+    // Extension repeats an existing id.
+    hoisted.state.extraQuestions = [
+      {
+        id: "budget",
+        section: "Constraints",
+        prompt: "Budget again?",
+        kind: "select",
+        required: true,
+        options: ["$"],
+      },
+    ];
+
+    const cfg = {
+      commands: { text: true },
+      agents: { defaults: { model: { primary: "openai/mock-1" } } },
+    } as ClawdbotConfig;
+
+    const result = await handleCommands(buildParams("/plan plan a trip", cfg));
+    expect(result.shouldContinue).toBe(false);
+
+    const createdDir = await getLatestPlanDir();
+    const questions = JSON.parse(
+      await fs.readFile(path.join(createdDir, "questions.json"), "utf-8"),
+    );
+    const ids = questions.questions.map((q: any) => q.id);
+    const uniqueIds = new Set(ids);
+    expect(uniqueIds.size).toBe(ids.length);
+  });
+
+  it("cancels cleanly if plan name prompt is cancelled", async () => {
+    (process.stdin as any).isTTY = true;
+    (process.stdout as any).isTTY = true;
+
+    hoisted.state.textQueue.push(CANCEL);
+
+    const cfg = {
+      commands: { text: true },
+      agents: { defaults: { model: { primary: "openai/mock-1" } } },
+    } as ClawdbotConfig;
+
+    const result = await handleCommands(buildParams("/plan plan a trip", cfg));
+    expect(result.shouldContinue).toBe(false);
+    expect(result.reply?.text).toContain("Cancelled");
+  });
+
+  it("errors on required multiselect when user selects nothing", async () => {
+    (process.stdin as any).isTTY = true;
+    (process.stdout as any).isTTY = true;
+
+    // Force extension with a required multiselect and accept it.
+    hoisted.state.confirmQueue.push(true);
+    hoisted.state.multiselectQueue.push([]);
+
+    const cfg = {
+      commands: { text: true },
+      agents: { defaults: { model: { primary: "openai/mock-1" } } },
+    } as ClawdbotConfig;
+
+    const result = await handleCommands(buildParams("/plan plan a trip", cfg));
+    expect(result.shouldContinue).toBe(false);
+    expect(result.reply?.text).toContain("Missing required answer");
+  });
+
+  it("does not run TUI handler when not in a TTY", async () => {
+    (process.stdin as any).isTTY = false;
+    (process.stdout as any).isTTY = false;
+
+    const cfg = {
+      commands: { text: true },
+      agents: { defaults: { model: { primary: "openai/mock-1" } } },
+    } as ClawdbotConfig;
+
+    const result = await handleCommands(buildParams("/plan plan a trip", cfg));
+    expect(result.shouldContinue).toBe(true);
+  });
+});

src/auto-reply/reply/commands-plan.ts

@@ -0,0 +1,491 @@
+import fs from "node:fs/promises";
+import path from "node:path";
+
+import { confirm, isCancel, select, text, multiselect } from "@clack/prompts";
+
+import type { ClawdbotPluginApi } from "../../plugins/types.js";
+import type { CommandHandler } from "./commands-types.js";
+
+// We import the llm-task tool directly (Clawdbot-native) so standalone TUI runs can
+// still use the agent's configured models via the embedded runner.
+import { createLlmTaskTool } from "../../../extensions/llm-task/src/llm-task-tool.js";
+
+type QuestionKind = "text" | "select" | "multiselect" | "confirm";
+
+export type QuestionSpec = {
+  id: string;
+  section: string;
+  prompt: string;
+  kind: QuestionKind;
+  required?: boolean;
+  options?: string[];
+  placeholder?: string;
+};
+
+type QuestionSet = {
+  title?: string;
+  goal: string;
+  questions: QuestionSpec[];
+};
+
+const QUESTIONS_SCHEMA = {
+  type: "object",
+  properties: {
+    title: { type: "string" },
+    goal: { type: "string" },
+    questions: {
+      type: "array",
+      items: {
+        type: "object",
+        properties: {
+          id: { type: "string" },
+          section: { type: "string" },
+          prompt: { type: "string" },
+          kind: { type: "string", enum: ["text", "select", "multiselect", "confirm"] },
+          required: { type: "boolean" },
+          options: { type: "array", items: { type: "string" } },
+          placeholder: { type: "string" },
+        },
+        required: ["id", "section", "prompt", "kind"],
+        additionalProperties: false,
+      },
+    },
+  },
+  required: ["goal", "questions"],
+  additionalProperties: false,
+};
+
+function slugify(input: string): string {
+  return input
+    .toLowerCase()
+    .replace(/[^a-z0-9]+/g, "-")
+    .replace(/^-+|-+$/g, "")
+    .slice(0, 60);
+}
+
+function nowStamp() {
+  const d = new Date();
+  const pad = (n: number) => String(n).padStart(2, "0");
+  return `${d.getFullYear()}-${pad(d.getMonth() + 1)}-${pad(d.getDate())}-${pad(d.getHours())}${pad(
+    d.getMinutes(),
+  )}`;
+}
+
+async function safeReadJson(filePath: string): Promise<any | null> {
+  try {
+    const text = await fs.readFile(filePath, "utf-8");
+    return JSON.parse(text);
+  } catch (err: any) {
+    if (err?.code === "ENOENT") return null;
+    return null;
+  }
+}
+
+async function writeJson(filePath: string, value: any) {
+  await fs.mkdir(path.dirname(filePath), { recursive: true });
+  await fs.writeFile(filePath, JSON.stringify(value, null, 2), "utf-8");
+}
+
+async function writeTextFile(filePath: string, textContent: string) {
+  await fs.mkdir(path.dirname(filePath), { recursive: true });
+  await fs.writeFile(filePath, textContent, "utf-8");
+}
+
+function buildLlmQuestionPrompt(goal: string) {
+  return (
+    `You are helping a user plan a project. Generate a compact questionnaire grouped into sections.\n` +
+    `Return JSON matching the provided schema.\n\n` +
+    `Requirements:\n` +
+    `- Ask only high-signal questions. Prefer multiple choice when the user can pick from common options.\n` +
+    `- Use sections like Goals, Constraints, Inputs, Outputs, Timeline, Risks (as appropriate).\n` +
+    `- Keep it to ~8-15 questions unless the goal clearly needs more.\n` +
+    `- Use stable ids (snake_case).\n` +
+    `- Use multiselect when multiple options may apply.\n\n` +
+    `GOAL:\n${goal}`
+  );
+}
+
+function buildLlmExtendPrompt(goal: string) {
+  return (
+    `You are helping a user plan a project.\n` +
+    `Given the current answers and existing question ids, propose any missing high-signal questions.\n` +
+    `Return JSON matching the provided schema.\n\n` +
+    `Rules:\n` +
+    `- If nothing important is missing, return {"goal": <same>, "questions": []}.\n` +
+    `- Do not repeat existing question ids.\n` +
+    `- Keep it short: up to 5 additional questions.\n\n` +
+    `GOAL:\n${goal}`
+  );
+}
+
+function buildPlanMarkdown(goal: string, answers: Record<string, any>, questions: QuestionSpec[]) {
+  const byId = new Map(questions.map((q) => [q.id, q] as const));
+  const sections = new Map<string, Array<{ q: QuestionSpec; a: any }>>();
+  for (const [id, a] of Object.entries(answers)) {
+    const q = byId.get(id);
+    if (!q) continue;
+    const list = sections.get(q.section) ?? [];
+    list.push({ q, a });
+    sections.set(q.section, list);
+  }
+
+  const lines: string[] = [];
+  lines.push(`# Plan\n\n## Goal\n${goal}\n`);
+  for (const [section, items] of sections) {
+    lines.push(`## ${section}`);
+    for (const { q, a } of items) {
+      const rendered = Array.isArray(a)
+        ? a.join(", ")
+        : typeof a === "boolean"
+          ? a
+            ? "yes"
+            : "no"
+          : String(a);
+      lines.push(`- **${q.prompt}**: ${rendered}`);
+    }
+    lines.push("");
+  }
+
+  return lines.join("\n").trim() + "\n";
+}
+
+function createFakePluginApi(cfg: any, workspaceDir: string): ClawdbotPluginApi {
+  // Minimal stub for llm-task tool; it only relies on `config` and `pluginConfig`.
+  return {
+    id: "local",
+    name: "local",
+    source: "internal",
+    config: cfg,
+    pluginConfig: {},
+    runtime: {} as any,
+    logger: {
+      info() {},
+      warn() {},
+      error() {},
+      debug() {},
+    },
+    registerTool() {},
+    registerHook() {},
+    registerHttpHandler() {},
+    registerChannel() {},
+    registerGatewayMethod() {},
+    registerCli() {},
+    registerService() {},
+    registerProvider() {},
+    registerCommand() {},
+    resolvePath: (input: string) => path.resolve(workspaceDir, input),
+    on() {},
+  } as any;
+}
+
+export const handlePlanCommand: CommandHandler = async (params, allowTextCommands) => {
+  if (!allowTextCommands) return null;
+
+  if (!params.command.commandBodyNormalized.startsWith("/plan")) return null;
+
+  // Only implement interactive plan builder in the local CLI.
+  const isInteractiveCli =
+    params.ctx.CommandSource === "cli" &&
+    Boolean(process.stdin.isTTY) &&
+    Boolean(process.stdout.isTTY);
+  if (!isInteractiveCli) return null;
+
+  const raw =
+    params.ctx.BodyForCommands ??
+    params.ctx.CommandBody ??
+    params.ctx.RawBody ??
+    params.ctx.BodyStripped ??
+    params.ctx.Body ??
+    "/plan";
+
+  const goal = raw.replace(/^\s*\/plan\s*/i, "").trim();
+  if (!goal) {
+    return {
+      shouldContinue: false,
+      reply: { text: "Usage: /plan <goal>" },
+    };
+  }
+
+  const defaultName = `${nowStamp()}-${slugify(goal.split(/\s+/).slice(0, 6).join(" ")) || "plan"}`;
+  const chosenName = await text({
+    message: "Plan name (folder under workspace/plans/)",
+    initialValue: defaultName,
+    validate: (v) => (!v?.trim() ? "Name required" : undefined),
+  });
+  if (isCancel(chosenName)) {
+    return { shouldContinue: false, reply: { text: "Cancelled." } };
+  }
+
+  const planName = slugify(String(chosenName).trim()) || defaultName;
+  const plansDir = path.join(params.workspaceDir, "plans");
+  const planDir = path.join(plansDir, planName);
+  await fs.mkdir(planDir, { recursive: true });
+
+  const metaPath = path.join(planDir, "meta.json");
+  const answersPath = path.join(planDir, "answers.json");
+  const planMdPath = path.join(planDir, "plan.md");
+
+  const existingAnswers = (await safeReadJson(answersPath)) ?? {};
+
+  await writeJson(metaPath, {
+    name: planName,
+    goal,
+    createdAt: new Date().toISOString(),
+    updatedAt: new Date().toISOString(),
+  });
+
+  // Ask the LLM to generate the question set.
+  const api = createFakePluginApi(params.cfg, params.workspaceDir);
+  const tool = createLlmTaskTool(api);
+
+  const llmResult = await tool.execute("llm-task", {
+    prompt: buildLlmQuestionPrompt(goal),
+    input: { goal, existingAnswers },
+    schema: QUESTIONS_SCHEMA,
+  });
+
+  const questionSet = (llmResult as any).details?.json as QuestionSet;
+  const questions: QuestionSpec[] = Array.isArray(questionSet?.questions)
+    ? questionSet.questions
+    : [];
+  if (questions.length === 0) {
+    return {
+      shouldContinue: false,
+      reply: { text: "No questions generated (unexpected)." },
+    };
+  }
+
+  const questionsPath = path.join(planDir, "questions.json");
+  await writeJson(questionsPath, { goal, questions });
+
+  // Group by section.
+  const sectionOrder: string[] = [];
+  const bySection = new Map<string, QuestionSpec[]>();
+  for (const q of questions) {
+    const section = q.section?.trim() || "General";
+    if (!bySection.has(section)) sectionOrder.push(section);
+    const list = bySection.get(section) ?? [];
+    list.push(q);
+    bySection.set(section, list);
+  }
+
+  const answers: Record<string, any> = { ...existingAnswers };
+
+  // Iterate sections with a review loop.
+  while (true) {
+    const section = await select({
+      message: "Choose a section",
+      options: [
+        ...sectionOrder.map((s) => ({ label: s, value: s })),
+        { label: "Review + finalize", value: "__review" },
+      ],
+    });
+    if (isCancel(section)) {
+      return { shouldContinue: false, reply: { text: "Cancelled." } };
+    }
+
+    if (section === "__review") break;
+
+    const qs = bySection.get(String(section)) ?? [];
+    for (const q of qs) {
+      const existing = answers[q.id];
+      const required = Boolean(q.required);
+
+      if (q.kind === "confirm") {
+        const res = await confirm({ message: q.prompt, initialValue: Boolean(existing ?? false) });
+        if (isCancel(res)) return { shouldContinue: false, reply: { text: "Cancelled." } };
+        answers[q.id] = Boolean(res);
+      } else if (q.kind === "select") {
+        const opts = (q.options ?? []).map((o) => ({ label: o, value: o }));
+        if (opts.length === 0) {
+          const res = await text({
+            message: q.prompt,
+            initialValue: existing ? String(existing) : "",
+          });
+          if (isCancel(res)) return { shouldContinue: false, reply: { text: "Cancelled." } };
+          const v = String(res).trim();
+          if (required && !v)
+            return { shouldContinue: false, reply: { text: `Missing required answer: ${q.id}` } };
+          answers[q.id] = v;
+        } else {
+          const res = await select({ message: q.prompt, options: opts });
+          if (isCancel(res)) return { shouldContinue: false, reply: { text: "Cancelled." } };
+          answers[q.id] = res;
+        }
+      } else if (q.kind === "multiselect") {
+        const opts = (q.options ?? []).map((o) => ({ label: o, value: o }));
+        if (opts.length === 0) {
+          const res = await text({
+            message: q.prompt,
+            initialValue: Array.isArray(existing) ? existing.join(", ") : "",
+            placeholder: q.placeholder,
+          });
+          if (isCancel(res)) return { shouldContinue: false, reply: { text: "Cancelled." } };
+          const arr = String(res)
+            .split(",")
+            .map((s) => s.trim())
+            .filter(Boolean);
+          if (required && arr.length === 0) {
+            return { shouldContinue: false, reply: { text: `Missing required answer: ${q.id}` } };
+          }
+          answers[q.id] = arr;
+        } else {
+          const res = await multiselect({
+            message: q.prompt,
+            options: opts,
+            required: required ? true : false,
+          } as any);
+          if (isCancel(res)) return { shouldContinue: false, reply: { text: "Cancelled." } };
+          const arr = Array.isArray(res) ? res : [];
+          if (required && arr.length === 0) {
+            return { shouldContinue: false, reply: { text: `Missing required answer: ${q.id}` } };
+          }
+          answers[q.id] = arr;
+        }
+      } else {
+        const res = await text({
+          message: q.prompt,
+          initialValue: existing ? String(existing) : "",
+          placeholder: q.placeholder,
+        });
+        if (isCancel(res)) return { shouldContinue: false, reply: { text: "Cancelled." } };
+        const v = String(res).trim();
+        if (required && !v) {
+          return { shouldContinue: false, reply: { text: `Missing required answer: ${q.id}` } };
+        }
+        answers[q.id] = v;
+      }
+
+      await writeJson(answersPath, answers);
+    }
+  }
+
+  // One-time dynamic extension at the end.
+  const existingIds = new Set(questions.map((q) => q.id));
+  const extend = await tool.execute("llm-task", {
+    prompt: buildLlmExtendPrompt(goal),
+    input: {
+      goal,
+      answers,
+      existingQuestionIds: Array.from(existingIds),
+    },
+    schema: QUESTIONS_SCHEMA,
+  });
+
+  const extendSet = (extend as any).details?.json as QuestionSet;
+  const extraQuestions: QuestionSpec[] = Array.isArray(extendSet?.questions)
+    ? extendSet.questions
+    : [];
+  const filteredExtras = extraQuestions.filter((q) => q && q.id && !existingIds.has(q.id));
+
+  if (filteredExtras.length > 0) {
+    const ok = await confirm({
+      message: `I have ${filteredExtras.length} more question(s) to tighten the plan. Add them?`,
+    });
+    if (!isCancel(ok) && ok === true) {
+      for (const q of filteredExtras) {
+        const section = q.section?.trim() || "General";
+        if (!bySection.has(section)) {
+          sectionOrder.push(section);
+          bySection.set(section, []);
+        }
+        bySection.get(section)!.push(q);
+        questions.push(q);
+        existingIds.add(q.id);
+      }
+
+      // Ask only the newly added questions (once).
+      for (const q of filteredExtras) {
+        const existing = answers[q.id];
+        const required = Boolean(q.required);
+
+        if (q.kind === "confirm") {
+          const res = await confirm({
+            message: q.prompt,
+            initialValue: Boolean(existing ?? false),
+          });
+          if (isCancel(res)) return { shouldContinue: false, reply: { text: "Cancelled." } };
+          answers[q.id] = Boolean(res);
+        } else if (q.kind === "select") {
+          const opts = (q.options ?? []).map((o) => ({ label: o, value: o }));
+          if (opts.length === 0) {
+            const res = await text({
+              message: q.prompt,
+              initialValue: existing ? String(existing) : "",
+            });
+            if (isCancel(res)) return { shouldContinue: false, reply: { text: "Cancelled." } };
+            const v = String(res).trim();
+            if (required && !v)
+              return { shouldContinue: false, reply: { text: `Missing required answer: ${q.id}` } };
+            answers[q.id] = v;
+          } else {
+            const res = await select({ message: q.prompt, options: opts });
+            if (isCancel(res)) return { shouldContinue: false, reply: { text: "Cancelled." } };
+            answers[q.id] = res;
+          }
+        } else if (q.kind === "multiselect") {
+          const opts = (q.options ?? []).map((o) => ({ label: o, value: o }));
+          if (opts.length === 0) {
+            const res = await text({
+              message: q.prompt,
+              initialValue: Array.isArray(existing) ? existing.join(", ") : "",
+            });
+            if (isCancel(res)) return { shouldContinue: false, reply: { text: "Cancelled." } };
+            const arr = String(res)
+              .split(",")
+              .map((s) => s.trim())
+              .filter(Boolean);
+            if (required && arr.length === 0)
+              return { shouldContinue: false, reply: { text: `Missing required answer: ${q.id}` } };
+            answers[q.id] = arr;
+          } else {
+            const res = await multiselect({
+              message: q.prompt,
+              options: opts,
+              required: required ? true : false,
+            } as any);
+            if (isCancel(res)) return { shouldContinue: false, reply: { text: "Cancelled." } };
+            const arr = Array.isArray(res) ? res : [];
+            if (required && arr.length === 0)
+              return { shouldContinue: false, reply: { text: `Missing required answer: ${q.id}` } };
+            answers[q.id] = arr;
+          }
+        } else {
+          const res = await text({
+            message: q.prompt,
+            initialValue: existing ? String(existing) : "",
+          });
+          if (isCancel(res)) return { shouldContinue: false, reply: { text: "Cancelled." } };
+          const v = String(res).trim();
+          if (required && !v)
+            return { shouldContinue: false, reply: { text: `Missing required answer: ${q.id}` } };
+          answers[q.id] = v;
+        }
+
+        await writeJson(answersPath, answers);
+      }
+
+      await writeJson(questionsPath, { goal, questions });
+    }
+  }
+
+  const md = buildPlanMarkdown(goal, answers, questions);
+  await writeTextFile(planMdPath, md);
+  await writeJson(metaPath, {
+    name: planName,
+    goal,
+    createdAt: (await safeReadJson(metaPath))?.createdAt ?? new Date().toISOString(),
+    updatedAt: new Date().toISOString(),
+  });
+
+  return {
+    shouldContinue: false,
+    reply: {
+      text:
+        `✅ Plan saved: ${planName}\n` +
+        `- ${path.relative(params.workspaceDir, planMdPath)}\n` +
+        `- ${path.relative(params.workspaceDir, answersPath)}\n\n` +
+        `Use /plans show ${planName} to view it.`,
+    },
+  };
+};

src/auto-reply/reply/commands-plans.ts

@@ -0,0 +1,256 @@
+import fs from "node:fs/promises";
+import path from "node:path";
+
+import { confirm, isCancel, select, text } from "@clack/prompts";
+
+import type { CommandHandler } from "./commands-types.js";
+
+type PlansArgs = {
+  action: "list" | "show" | "rename" | "trash" | "help";
+  a?: string;
+  b?: string;
+};
+
+function parsePlansArgs(raw: string): PlansArgs {
+  const trimmed = raw.trim();
+  const parts = trimmed.split(/\s+/).filter(Boolean);
+  const cmd = parts[0]?.toLowerCase();
+  if (cmd !== "/plans") return { action: "help" };
+  const sub = parts[1]?.toLowerCase();
+  if (!sub || sub === "list") return { action: "list" };
+  if (sub === "help") return { action: "help" };
+  if (sub === "show") return { action: "show", a: parts[2] };
+  if (sub === "rename") return { action: "rename", a: parts[2], b: parts[3] };
+  if (sub === "trash" || sub === "delete" || sub === "rm") return { action: "trash", a: parts[2] };
+  // Default: treat unknown as help.
+  return { action: "help" };
+}
+
+async function listPlanDirs(plansDir: string): Promise<string[]> {
+  try {
+    const entries = await fs.readdir(plansDir, { withFileTypes: true });
+    return entries
+      .filter((e) => e.isDirectory())
+      .map((e) => e.name)
+      .filter((name) => !name.startsWith("."))
+      .sort();
+  } catch (err: any) {
+    if (err?.code === "ENOENT") return [];
+    throw err;
+  }
+}
+
+async function readFirstExisting(paths: string[]): Promise<string | null> {
+  for (const p of paths) {
+    try {
+      const text = await fs.readFile(p, "utf-8");
+      return text;
+    } catch (err: any) {
+      if (err?.code === "ENOENT") continue;
+      throw err;
+    }
+  }
+  return null;
+}
+
+export const handlePlansCommand: CommandHandler = async (params, allowTextCommands) => {
+  if (!allowTextCommands) return null;
+
+  // Match on normalized command body
+  if (!params.command.commandBodyNormalized.startsWith("/plans")) return null;
+
+  const raw =
+    params.ctx.BodyForCommands ??
+    params.ctx.CommandBody ??
+    params.ctx.RawBody ??
+    params.ctx.BodyStripped ??
+    params.ctx.Body ??
+    "/plans";
+
+  const args = parsePlansArgs(raw);
+
+  const plansDir = path.join(params.workspaceDir, "plans");
+
+  const isInteractiveCli =
+    params.ctx.CommandSource === "cli" &&
+    Boolean(process.stdin.isTTY) &&
+    Boolean(process.stdout.isTTY);
+
+  if (args.action === "help") {
+    return {
+      shouldContinue: false,
+      reply: {
+        text:
+          "Usage:\n" +
+          "  /plans list\n" +
+          "  /plans show <name>\n" +
+          "  /plans rename <old> <new>\n" +
+          "  /plans trash <name>\n\n" +
+          "TUI:\n" +
+          "  /plans (with no args) opens an interactive picker in the CLI.\n\n" +
+          "Notes:\n" +
+          "- Plans are stored under workspace/plans/.\n" +
+          "- Use /plan <goal> to start a new plan; /plans helps manage saved plan folders.",
+      },
+    };
+  }
+
+  if (args.action === "list") {
+    const names = await listPlanDirs(plansDir);
+    if (names.length === 0) {
+      return {
+        shouldContinue: false,
+        reply: { text: "No plans found yet. Create one with: /plan <goal>" },
+      };
+    }
+
+    // Interactive picker only when running in the CLI TUI.
+    // For chat channels (Discord/Telegram/etc.), return plain text.
+    const wantsInteractive =
+      isInteractiveCli && (raw.trim() === "/plans" || raw.trim() === "/plans list");
+    if (wantsInteractive) {
+      const selected = await select({
+        message: "Select a plan",
+        options: names
+          .slice()
+          .reverse()
+          .map((n) => ({ label: n, value: n })),
+      });
+      if (isCancel(selected)) {
+        return { shouldContinue: false, reply: { text: "Cancelled." } };
+      }
+
+      const planName = String(selected);
+      const action = await select({
+        message: `Action for ${planName}`,
+        options: [
+          { label: "Show", value: "show" },
+          { label: "Rename", value: "rename" },
+          { label: "Trash", value: "trash" },
+        ],
+      });
+      if (isCancel(action)) {
+        return { shouldContinue: false, reply: { text: "Cancelled." } };
+      }
+
+      if (action === "show") {
+        const planDir = path.join(plansDir, planName);
+        const planMd = await readFirstExisting([
+          path.join(planDir, "plan.md"),
+          path.join(planDir, "README.md"),
+        ]);
+        if (!planMd) {
+          return {
+            shouldContinue: false,
+            reply: { text: `No plan.md found for '${planName}'. Looked in: ${planDir}` },
+          };
+        }
+        const trimmed = planMd.trim();
+        const preview =
+          trimmed.length > 6000 ? `${trimmed.slice(0, 6000)}\n\n…(truncated)` : trimmed;
+        return { shouldContinue: false, reply: { text: `Plan: ${planName}\n\n${preview}` } };
+      }
+
+      if (action === "rename") {
+        const next = await text({
+          message: `Rename '${planName}' to:`,
+          initialValue: planName,
+          validate: (v) => (!v?.trim() ? "Name required" : undefined),
+        });
+        if (isCancel(next)) return { shouldContinue: false, reply: { text: "Cancelled." } };
+        const toName = String(next).trim();
+        if (toName && toName !== planName) {
+          await fs.rename(path.join(plansDir, planName), path.join(plansDir, toName));
+        }
+        return {
+          shouldContinue: false,
+          reply: { text: `Renamed plan '${planName}' → '${toName}'.` },
+        };
+      }
+
+      if (action === "trash") {
+        const ok = await confirm({ message: `Move '${planName}' to trash?` });
+        if (isCancel(ok) || ok === false) {
+          return { shouldContinue: false, reply: { text: "Cancelled." } };
+        }
+        const fromDir = path.join(plansDir, planName);
+        const trashDir = path.join(plansDir, ".trash");
+        await fs.mkdir(trashDir, { recursive: true });
+        const stamped = `${planName}__${new Date().toISOString().replace(/[:.]/g, "-")}`;
+        const toDir = path.join(trashDir, stamped);
+        await fs.rename(fromDir, toDir);
+        return { shouldContinue: false, reply: { text: `Moved plan '${planName}' to trash.` } };
+      }
+    }
+
+    const lines = ["Plans:", ...names.map((n) => `- ${n}`), "", "Tip: /plans show <name>"];
+    return { shouldContinue: false, reply: { text: lines.join("\n") } };
+  }
+
+  if (args.action === "show") {
+    const name = String(args.a ?? "").trim();
+    if (!name) {
+      return { shouldContinue: false, reply: { text: "Usage: /plans show <name>" } };
+    }
+
+    const planDir = path.join(plansDir, name);
+    const planMd = await readFirstExisting([
+      path.join(planDir, "plan.md"),
+      path.join(planDir, "README.md"),
+    ]);
+
+    if (!planMd) {
+      return {
+        shouldContinue: false,
+        reply: { text: `No plan.md found for '${name}'. Looked in: ${planDir}` },
+      };
+    }
+
+    const trimmed = planMd.trim();
+    const preview = trimmed.length > 1800 ? `${trimmed.slice(0, 1800)}\n\n…(truncated)` : trimmed;
+    return {
+      shouldContinue: false,
+      reply: { text: `Plan: ${name}\n\n${preview}` },
+    };
+  }
+
+  if (args.action === "rename") {
+    const from = String(args.a ?? "").trim();
+    const to = String(args.b ?? "").trim();
+    if (!from || !to) {
+      return { shouldContinue: false, reply: { text: "Usage: /plans rename <old> <new>" } };
+    }
+    const fromDir = path.join(plansDir, from);
+    const toDir = path.join(plansDir, to);
+
+    await fs.mkdir(plansDir, { recursive: true });
+    await fs.rename(fromDir, toDir);
+
+    return {
+      shouldContinue: false,
+      reply: { text: `Renamed plan '${from}' → '${to}'.` },
+    };
+  }
+
+  if (args.action === "trash") {
+    const name = String(args.a ?? "").trim();
+    if (!name) {
+      return { shouldContinue: false, reply: { text: "Usage: /plans trash <name>" } };
+    }
+
+    const fromDir = path.join(plansDir, name);
+    const trashDir = path.join(plansDir, ".trash");
+    await fs.mkdir(trashDir, { recursive: true });
+
+    const stamped = `${name}__${new Date().toISOString().replace(/[:.]/g, "-")}`;
+    const toDir = path.join(trashDir, stamped);
+    await fs.rename(fromDir, toDir);
+
+    return {
+      shouldContinue: false,
+      reply: { text: `Moved plan '${name}' to trash.` },
+    };
+  }
+
+  return null;
+};

src/auto-reply/reply/commands.test.ts

@@ -132,6 +132,44 @@ describe("handleCommands gating", () => {
   });
 });
 
+describe("/plans", () => {
+  it("lists plan directories", async () => {
+    const cfg = {
+      commands: { text: true },
+      whatsapp: { allowFrom: ["*"] },
+    } as ClawdbotConfig;
+
+    const plansDir = path.join(testWorkspaceDir, "plans");
+    await fs.mkdir(path.join(plansDir, "2026-01-24-trip"), { recursive: true });
+    await fs.writeFile(
+      path.join(plansDir, "2026-01-24-trip", "plan.md"),
+      "# Trip Plan\n\nDo stuff\n",
+      "utf-8",
+    );
+
+    const params = buildParams("/plans list", cfg);
+    const result = await handleCommands(params);
+    expect(result.shouldContinue).toBe(false);
+    expect(result.reply?.text).toContain("2026-01-24-trip");
+  });
+
+  it("shows plan.md", async () => {
+    const cfg = {
+      commands: { text: true },
+      whatsapp: { allowFrom: ["*"] },
+    } as ClawdbotConfig;
+
+    const plansDir = path.join(testWorkspaceDir, "plans");
+    await fs.mkdir(path.join(plansDir, "demo"), { recursive: true });
+    await fs.writeFile(path.join(plansDir, "demo", "plan.md"), "Hello plan", "utf-8");
+
+    const params = buildParams("/plans show demo", cfg);
+    const result = await handleCommands(params);
+    expect(result.shouldContinue).toBe(false);
+    expect(result.reply?.text).toContain("Hello plan");
+  });
+});
+
 describe("handleCommands bash alias", () => {
   it("routes !poll through the /bash handler", async () => {
     resetBashChatCommandForTests();

src/channels/plugins/outbound/telegram.test.ts

@@ -0,0 +1,81 @@
+import { describe, expect, it, vi } from "vitest";
+
+import type { ClawdbotConfig } from "../../../config/config.js";
+import { telegramOutbound } from "./telegram.js";
+
+describe("telegramOutbound.sendPayload", () => {
+  it("sends text payload with buttons", async () => {
+    const sendTelegram = vi.fn(async () => ({ messageId: "m1", chatId: "c1" }));
+
+    const result = await telegramOutbound.sendPayload?.({
+      cfg: {} as ClawdbotConfig,
+      to: "telegram:123",
+      text: "ignored",
+      payload: {
+        text: "Hello",
+        channelData: {
+          telegram: {
+            buttons: [[{ text: "Option", callback_data: "/option" }]],
+          },
+        },
+      },
+      deps: { sendTelegram },
+    });
+
+    expect(sendTelegram).toHaveBeenCalledTimes(1);
+    expect(sendTelegram).toHaveBeenCalledWith(
+      "telegram:123",
+      "Hello",
+      expect.objectContaining({
+        buttons: [[{ text: "Option", callback_data: "/option" }]],
+        textMode: "html",
+      }),
+    );
+    expect(result).toEqual({ channel: "telegram", messageId: "m1", chatId: "c1" });
+  });
+
+  it("sends media payloads and attaches buttons only to first", async () => {
+    const sendTelegram = vi
+      .fn()
+      .mockResolvedValueOnce({ messageId: "m1", chatId: "c1" })
+      .mockResolvedValueOnce({ messageId: "m2", chatId: "c1" });
+
+    const result = await telegramOutbound.sendPayload?.({
+      cfg: {} as ClawdbotConfig,
+      to: "telegram:123",
+      text: "ignored",
+      payload: {
+        text: "Caption",
+        mediaUrls: ["https://example.com/a.png", "https://example.com/b.png"],
+        channelData: {
+          telegram: {
+            buttons: [[{ text: "Go", callback_data: "/go" }]],
+          },
+        },
+      },
+      deps: { sendTelegram },
+    });
+
+    expect(sendTelegram).toHaveBeenCalledTimes(2);
+    expect(sendTelegram).toHaveBeenNthCalledWith(
+      1,
+      "telegram:123",
+      "Caption",
+      expect.objectContaining({
+        mediaUrl: "https://example.com/a.png",
+        buttons: [[{ text: "Go", callback_data: "/go" }]],
+      }),
+    );
+    const secondOpts = sendTelegram.mock.calls[1]?.[2] as { buttons?: unknown } | undefined;
+    expect(sendTelegram).toHaveBeenNthCalledWith(
+      2,
+      "telegram:123",
+      "",
+      expect.objectContaining({
+        mediaUrl: "https://example.com/b.png",
+      }),
+    );
+    expect(secondOpts?.buttons).toBeUndefined();
+    expect(result).toEqual({ channel: "telegram", messageId: "m2", chatId: "c1" });
+  });
+});

src/channels/plugins/outbound/telegram.ts

@@ -18,6 +18,7 @@ function parseThreadId(threadId?: string | number | null) {
   const parsed = Number.parseInt(trimmed, 10);
   return Number.isFinite(parsed) ? parsed : undefined;
 }
+
 export const telegramOutbound: ChannelOutboundAdapter = {
   deliveryMode: "direct",
   chunker: markdownToTelegramHtmlChunks,
@@ -50,4 +51,46 @@ export const telegramOutbound: ChannelOutboundAdapter = {
     });
     return { channel: "telegram", ...result };
   },
+  sendPayload: async ({ to, payload, accountId, deps, replyToId, threadId }) => {
+    const send = deps?.sendTelegram ?? sendMessageTelegram;
+    const replyToMessageId = parseReplyToMessageId(replyToId);
+    const messageThreadId = parseThreadId(threadId);
+    const telegramData = payload.channelData?.telegram as
+      | { buttons?: Array<Array<{ text: string; callback_data: string }>> }
+      | undefined;
+    const text = payload.text ?? "";
+    const mediaUrls = payload.mediaUrls?.length
+      ? payload.mediaUrls
+      : payload.mediaUrl
+        ? [payload.mediaUrl]
+        : [];
+    const baseOpts = {
+      verbose: false,
+      textMode: "html" as const,
+      messageThreadId,
+      replyToMessageId,
+      accountId: accountId ?? undefined,
+    };
+
+    if (mediaUrls.length === 0) {
+      const result = await send(to, text, {
+        ...baseOpts,
+        buttons: telegramData?.buttons,
+      });
+      return { channel: "telegram", ...result };
+    }
+
+    // Telegram allows reply_markup on media; attach buttons only to first send.
+    let finalResult: Awaited<ReturnType<typeof send>> | undefined;
+    for (let i = 0; i < mediaUrls.length; i += 1) {
+      const mediaUrl = mediaUrls[i];
+      const isFirst = i === 0;
+      finalResult = await send(to, isFirst ? text : "", {
+        ...baseOpts,
+        mediaUrl,
+        ...(isFirst ? { buttons: telegramData?.buttons } : {}),
+      });
+    }
+    return { channel: "telegram", ...(finalResult ?? { messageId: "unknown", chatId: to }) };
+  },
 };

src/cli/program/register.onboard.ts

@@ -78,7 +78,7 @@ export function registerOnboardCommand(program: Command) {
     .option("--opencode-zen-api-key <key>", "OpenCode Zen API key")
     .option("--gateway-port <port>", "Gateway port")
     .option("--gateway-bind <mode>", "Gateway bind: loopback|tailnet|lan|auto|custom")
-    .option("--gateway-auth <mode>", "Gateway auth: off|token|password")
+    .option("--gateway-auth <mode>", "Gateway auth: token|password")
     .option("--gateway-token <token>", "Gateway token (token auth)")
     .option("--gateway-password <password>", "Gateway password (password auth)")
     .option("--remote-url <url>", "Remote Gateway WebSocket URL")

src/commands/configure.gateway-auth.test.ts

@@ -3,26 +3,18 @@ import { describe, expect, it } from "vitest";
 import { buildGatewayAuthConfig } from "./configure.js";
 
 describe("buildGatewayAuthConfig", () => {
-  it("clears token/password when auth is off", () => {
-    const result = buildGatewayAuthConfig({
-      existing: { mode: "token", token: "abc", password: "secret" },
-      mode: "off",
-    });
-
-    expect(result).toBeUndefined();
-  });
-
-  it("preserves allowTailscale when auth is off", () => {
+  it("preserves allowTailscale when switching to token", () => {
     const result = buildGatewayAuthConfig({
       existing: {
-        mode: "token",
-        token: "abc",
+        mode: "password",
+        password: "secret",
         allowTailscale: true,
       },
-      mode: "off",
+      mode: "token",
+      token: "abc",
     });
 
-    expect(result).toEqual({ allowTailscale: true });
+    expect(result).toEqual({ mode: "token", token: "abc", allowTailscale: true });
   });
 
   it("drops password when switching to token", () => {

src/commands/configure.gateway-auth.ts

@@ -12,7 +12,7 @@ import {
   promptModelAllowlist,
 } from "./model-picker.js";
 
-type GatewayAuthChoice = "off" | "token" | "password";
+type GatewayAuthChoice = "token" | "password";
 
 const ANTHROPIC_OAUTH_MODEL_KEYS = [
   "anthropic/claude-opus-4-5",
@@ -30,9 +30,6 @@ export function buildGatewayAuthConfig(params: {
   const base: GatewayAuthConfig = {};
   if (typeof allowTailscale === "boolean") base.allowTailscale = allowTailscale;
 
-  if (params.mode === "off") {
-    return Object.keys(base).length > 0 ? base : undefined;
-  }
   if (params.mode === "token") {
     return { ...base, mode: "token", token: params.token };
   }

src/commands/configure.gateway.ts

@@ -7,7 +7,7 @@ import { buildGatewayAuthConfig } from "./configure.gateway-auth.js";
 import { confirm, select, text } from "./configure.shared.js";
 import { guardCancel, randomToken } from "./onboard-helpers.js";
 
-type GatewayAuthChoice = "off" | "token" | "password";
+type GatewayAuthChoice = "token" | "password";
 
 export async function promptGatewayConfig(
   cfg: ClawdbotConfig,
@@ -91,11 +91,6 @@ export async function promptGatewayConfig(
     await select({
       message: "Gateway auth",
       options: [
-        {
-          value: "off",
-          label: "Off (loopback only)",
-          hint: "Not recommended unless you fully trust local processes",
-        },
         { value: "token", label: "Token", hint: "Recommended default" },
         { value: "password", label: "Password" },
       ],
@@ -165,11 +160,6 @@ export async function promptGatewayConfig(
     bind = "loopback";
   }
 
-  if (authMode === "off" && bind !== "loopback") {
-    note("Non-loopback bind requires auth. Switching to token auth.", "Note");
-    authMode = "token";
-  }
-
   if (tailscaleMode === "funnel" && authMode !== "password") {
     note("Tailscale funnel requires password auth.", "Note");
     authMode = "password";

src/commands/onboard-non-interactive.gateway.test.ts

@@ -210,7 +210,7 @@ describe("onboard (non-interactive): gateway and remote auth", () => {
     await fs.rm(stateDir, { recursive: true, force: true });
   }, 60_000);
 
-  it("auto-enables token auth when binding LAN and persists the token", async () => {
+  it("auto-generates token auth when binding LAN and persists the token", async () => {
     if (process.platform === "win32") {
       // Windows runner occasionally drops the temp config write in this flow; skip to keep CI green.
       return;
@@ -242,7 +242,6 @@ describe("onboard (non-interactive): gateway and remote auth", () => {
         installDaemon: false,
         gatewayPort: port,
         gatewayBind: "lan",
-        gatewayAuth: "off",
       },
       runtime,
     );

src/commands/onboard-non-interactive/local/gateway-config.ts

@@ -28,16 +28,20 @@ export function applyNonInteractiveGatewayConfig(params: {
 
   const port = hasGatewayPort ? (opts.gatewayPort as number) : params.defaultPort;
   let bind = opts.gatewayBind ?? "loopback";
-  let authMode = opts.gatewayAuth ?? "token";
+  const authModeRaw = opts.gatewayAuth ?? "token";
+  if (authModeRaw !== "token" && authModeRaw !== "password") {
+    runtime.error("Invalid --gateway-auth (use token|password).");
+    runtime.exit(1);
+    return null;
+  }
+  let authMode = authModeRaw;
   const tailscaleMode = opts.tailscale ?? "off";
   const tailscaleResetOnExit = Boolean(opts.tailscaleResetOnExit);
 
   // Tighten config to safe combos:
   // - If Tailscale is on, force loopback bind (the tunnel handles external access).
-  // - If binding beyond loopback, disallow auth=off.
   // - If using Tailscale Funnel, require password auth.
   if (tailscaleMode !== "off" && bind !== "loopback") bind = "loopback";
-  if (authMode === "off" && bind !== "loopback") authMode = "token";
   if (tailscaleMode === "funnel" && authMode !== "password") authMode = "password";
 
   let nextConfig = params.nextConfig;

src/commands/onboard-types.ts

@@ -32,7 +32,7 @@ export type AuthChoice =
   | "copilot-proxy"
   | "qwen-portal"
   | "skip";
-export type GatewayAuthChoice = "off" | "token" | "password";
+export type GatewayAuthChoice = "token" | "password";
 export type ResetScope = "config" | "config+creds+sessions" | "full";
 export type GatewayBind = "loopback" | "lan" | "auto" | "custom" | "tailnet";
 export type TailscaleMode = "off" | "serve" | "funnel";

src/config/schema.ts

@@ -199,6 +199,7 @@ const FIELD_LABELS: Record<string, string> = {
   "tools.web.fetch.userAgent": "Web Fetch User-Agent",
   "gateway.controlUi.basePath": "Control UI Base Path",
   "gateway.controlUi.allowInsecureAuth": "Allow Insecure Control UI Auth",
+  "gateway.controlUi.dangerouslyDisableDeviceAuth": "Dangerously Disable Control UI Device Auth",
   "gateway.http.endpoints.chatCompletions.enabled": "OpenAI Chat Completions Endpoint",
   "gateway.reload.mode": "Config Reload Mode",
   "gateway.reload.debounceMs": "Config Reload Debounce (ms)",
@@ -381,6 +382,8 @@ const FIELD_HELP: Record<string, string> = {
     "Optional URL prefix where the Control UI is served (e.g. /clawdbot).",
   "gateway.controlUi.allowInsecureAuth":
     "Allow Control UI auth over insecure HTTP (token-only; not recommended).",
+  "gateway.controlUi.dangerouslyDisableDeviceAuth":
+    "DANGEROUS. Disable Control UI device identity checks (token/password only).",
   "gateway.http.endpoints.chatCompletions.enabled":
     "Enable the OpenAI-compatible `POST /v1/chat/completions` endpoint (default: false).",
   "gateway.reload.mode": 'Hot reload strategy for config changes ("hybrid" recommended).',

src/config/types.gateway.ts

@@ -66,6 +66,8 @@ export type GatewayControlUiConfig = {
   basePath?: string;
   /** Allow token-only auth over insecure HTTP (default: false). */
   allowInsecureAuth?: boolean;
+  /** DANGEROUS: Disable device identity checks for the Control UI (default: false). */
+  dangerouslyDisableDeviceAuth?: boolean;
 };
 
 export type GatewayAuthMode = "token" | "password";

src/config/zod-schema.ts

@@ -319,6 +319,7 @@ export const ClawdbotSchema = z
             enabled: z.boolean().optional(),
             basePath: z.string().optional(),
             allowInsecureAuth: z.boolean().optional(),
+            dangerouslyDisableDeviceAuth: z.boolean().optional(),
           })
           .strict()
           .optional(),

src/gateway/server.auth.e2e.test.ts

@@ -352,6 +352,53 @@ describe("gateway server auth/connect", () => {
     }
   });
 
+  test("allows control ui with stale device identity when device auth is disabled", async () => {
+    testState.gatewayControlUi = { dangerouslyDisableDeviceAuth: true };
+    const prevToken = process.env.CLAWDBOT_GATEWAY_TOKEN;
+    process.env.CLAWDBOT_GATEWAY_TOKEN = "secret";
+    const port = await getFreePort();
+    const server = await startGatewayServer(port);
+    const ws = await openWs(port);
+    const { loadOrCreateDeviceIdentity, publicKeyRawBase64UrlFromPem, signDevicePayload } =
+      await import("../infra/device-identity.js");
+    const identity = loadOrCreateDeviceIdentity();
+    const signedAtMs = Date.now() - 60 * 60 * 1000;
+    const payload = buildDeviceAuthPayload({
+      deviceId: identity.deviceId,
+      clientId: GATEWAY_CLIENT_NAMES.CONTROL_UI,
+      clientMode: GATEWAY_CLIENT_MODES.WEBCHAT,
+      role: "operator",
+      scopes: [],
+      signedAtMs,
+      token: "secret",
+    });
+    const device = {
+      id: identity.deviceId,
+      publicKey: publicKeyRawBase64UrlFromPem(identity.publicKeyPem),
+      signature: signDevicePayload(identity.privateKeyPem, payload),
+      signedAt: signedAtMs,
+    };
+    const res = await connectReq(ws, {
+      token: "secret",
+      device,
+      client: {
+        id: GATEWAY_CLIENT_NAMES.CONTROL_UI,
+        version: "1.0.0",
+        platform: "web",
+        mode: GATEWAY_CLIENT_MODES.WEBCHAT,
+      },
+    });
+    expect(res.ok).toBe(true);
+    expect((res.payload as { auth?: unknown } | undefined)?.auth).toBeUndefined();
+    ws.close();
+    await server.close();
+    if (prevToken === undefined) {
+      delete process.env.CLAWDBOT_GATEWAY_TOKEN;
+    } else {
+      process.env.CLAWDBOT_GATEWAY_TOKEN = prevToken;
+    }
+  });
+
   test("rejects proxied connections without auth when proxy headers are untrusted", async () => {
     testState.gatewayAuth = { mode: "none" };
     const prevToken = process.env.CLAWDBOT_GATEWAY_TOKEN;

src/gateway/server/ws-connection/message-handler.ts

@@ -335,7 +335,7 @@ export function attachGatewayWsMessageHandler(params: {
         connectParams.role = role;
         connectParams.scopes = scopes;
 
-        const device = connectParams.device;
+        const deviceRaw = connectParams.device;
         let devicePublicKey: string | null = null;
         const hasTokenAuth = Boolean(connectParams.auth?.token);
         const hasPasswordAuth = Boolean(connectParams.auth?.password);
@@ -343,6 +343,10 @@ export function attachGatewayWsMessageHandler(params: {
         const isControlUi = connectParams.client.id === GATEWAY_CLIENT_IDS.CONTROL_UI;
         const allowInsecureControlUi =
           isControlUi && configSnapshot.gateway?.controlUi?.allowInsecureAuth === true;
+        const disableControlUiDeviceAuth =
+          isControlUi && configSnapshot.gateway?.controlUi?.dangerouslyDisableDeviceAuth === true;
+        const allowControlUiBypass = allowInsecureControlUi || disableControlUiDeviceAuth;
+        const device = disableControlUiDeviceAuth ? null : deviceRaw;
         if (hasUntrustedProxyHeaders && resolvedAuth.mode === "none") {
           setHandshakeState("failed");
           setCloseCause("proxy-auth-required", {
@@ -370,9 +374,9 @@ export function attachGatewayWsMessageHandler(params: {
         }
 
         if (!device) {
-          const canSkipDevice = allowInsecureControlUi ? hasSharedAuth : hasTokenAuth;
+          const canSkipDevice = allowControlUiBypass ? hasSharedAuth : hasTokenAuth;
 
-          if (isControlUi && !allowInsecureControlUi) {
+          if (isControlUi && !allowControlUiBypass) {
             const errorMessage = "control ui requires HTTPS or localhost (secure context)";
             setHandshakeState("failed");
             setCloseCause("control-ui-insecure-auth", {
@@ -615,7 +619,7 @@ export function attachGatewayWsMessageHandler(params: {
           return;
         }
 
-        const skipPairing = allowInsecureControlUi && hasSharedAuth;
+        const skipPairing = allowControlUiBypass && hasSharedAuth;
         if (device && devicePublicKey && !skipPairing) {
           const requirePairing = async (reason: string, _paired?: { deviceId: string }) => {
             const pairing = await requestDevicePairing({
@@ -736,9 +740,7 @@ export function attachGatewayWsMessageHandler(params: {
         const shouldTrackPresence = !isGatewayCliClient(connectParams.client);
         const clientId = connectParams.client.id;
         const instanceId = connectParams.client.instanceId;
-        const presenceKey = shouldTrackPresence
-          ? (connectParams.device?.id ?? instanceId ?? connId)
-          : undefined;
+        const presenceKey = shouldTrackPresence ? (device?.id ?? instanceId ?? connId) : undefined;
 
         logWs("in", "connect", {
           connId,
@@ -766,10 +768,10 @@ export function attachGatewayWsMessageHandler(params: {
             deviceFamily: connectParams.client.deviceFamily,
             modelIdentifier: connectParams.client.modelIdentifier,
             mode: connectParams.client.mode,
-            deviceId: connectParams.device?.id,
+            deviceId: device?.id,
             roles: [role],
             scopes,
-            instanceId: connectParams.device?.id ?? instanceId,
+            instanceId: device?.id ?? instanceId,
             reason: "connect",
           });
           incrementPresenceVersion();

src/plugin-sdk/index.ts

@@ -63,6 +63,11 @@ export type {
   ClawdbotPluginService,
   ClawdbotPluginServiceContext,
 } from "../plugins/types.js";
+export type {
+  GatewayRequestHandler,
+  GatewayRequestHandlerOptions,
+  RespondFn,
+} from "../gateway/server-methods/types.js";
 export type { PluginRuntime } from "../plugins/runtime/types.js";
 export { normalizePluginHttpPath } from "../plugins/http-path.js";
 export { registerPluginHttpRoute } from "../plugins/http-registry.js";

src/security/audit.test.ts

@@ -293,7 +293,30 @@ describe("security audit", () => {
       expect.arrayContaining([
         expect.objectContaining({
           checkId: "gateway.control_ui.insecure_auth",
-          severity: "warn",
+          severity: "critical",
+        }),
+      ]),
+    );
+  });
+
+  it("warns when control UI device auth is disabled", async () => {
+    const cfg: ClawdbotConfig = {
+      gateway: {
+        controlUi: { dangerouslyDisableDeviceAuth: true },
+      },
+    };
+
+    const res = await runSecurityAudit({
+      config: cfg,
+      includeFilesystem: false,
+      includeChannelSecurity: false,
+    });
+
+    expect(res.findings).toEqual(
+      expect.arrayContaining([
+        expect.objectContaining({
+          checkId: "gateway.control_ui.device_auth_disabled",
+          severity: "critical",
         }),
       ]),
     );

src/security/audit.ts

@@ -274,7 +274,7 @@ function collectGatewayConfigFindings(cfg: ClawdbotConfig): SecurityAuditFinding
   if (cfg.gateway?.controlUi?.allowInsecureAuth === true) {
     findings.push({
       checkId: "gateway.control_ui.insecure_auth",
-      severity: "warn",
+      severity: "critical",
       title: "Control UI allows insecure HTTP auth",
       detail:
         "gateway.controlUi.allowInsecureAuth=true allows token-only auth over HTTP and skips device identity.",
@@ -282,6 +282,17 @@ function collectGatewayConfigFindings(cfg: ClawdbotConfig): SecurityAuditFinding
     });
   }
 
+  if (cfg.gateway?.controlUi?.dangerouslyDisableDeviceAuth === true) {
+    findings.push({
+      checkId: "gateway.control_ui.device_auth_disabled",
+      severity: "critical",
+      title: "DANGEROUS: Control UI device auth disabled",
+      detail:
+        "gateway.controlUi.dangerouslyDisableDeviceAuth=true disables device identity checks for the Control UI.",
+      remediation: "Disable it unless you are in a short-lived break-glass scenario.",
+    });
+  }
+
   const token =
     typeof auth.token === "string" && auth.token.trim().length > 0 ? auth.token.trim() : null;
   if (auth.mode === "token" && token && token.length < 24) {

src/slack/monitor/media.test.ts

@@ -0,0 +1,278 @@
+import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
+
+// Store original fetch
+const originalFetch = globalThis.fetch;
+let mockFetch: ReturnType<typeof vi.fn>;
+
+describe("fetchWithSlackAuth", () => {
+  beforeEach(() => {
+    // Create a new mock for each test
+    mockFetch = vi.fn();
+    globalThis.fetch = mockFetch as typeof fetch;
+  });
+
+  afterEach(() => {
+    // Restore original fetch
+    globalThis.fetch = originalFetch;
+    vi.resetModules();
+  });
+
+  it("sends Authorization header on initial request with manual redirect", async () => {
+    // Import after mocking fetch
+    const { fetchWithSlackAuth } = await import("./media.js");
+
+    // Simulate direct 200 response (no redirect)
+    const mockResponse = new Response(Buffer.from("image data"), {
+      status: 200,
+      headers: { "content-type": "image/jpeg" },
+    });
+    mockFetch.mockResolvedValueOnce(mockResponse);
+
+    const result = await fetchWithSlackAuth("https://files.slack.com/test.jpg", "xoxb-test-token");
+
+    expect(result).toBe(mockResponse);
+
+    // Verify fetch was called with correct params
+    expect(mockFetch).toHaveBeenCalledTimes(1);
+    expect(mockFetch).toHaveBeenCalledWith("https://files.slack.com/test.jpg", {
+      headers: { Authorization: "Bearer xoxb-test-token" },
+      redirect: "manual",
+    });
+  });
+
+  it("follows redirects without Authorization header", async () => {
+    const { fetchWithSlackAuth } = await import("./media.js");
+
+    // First call: redirect response from Slack
+    const redirectResponse = new Response(null, {
+      status: 302,
+      headers: { location: "https://cdn.slack-edge.com/presigned-url?sig=abc123" },
+    });
+
+    // Second call: actual file content from CDN
+    const fileResponse = new Response(Buffer.from("actual image data"), {
+      status: 200,
+      headers: { "content-type": "image/jpeg" },
+    });
+
+    mockFetch.mockResolvedValueOnce(redirectResponse).mockResolvedValueOnce(fileResponse);
+
+    const result = await fetchWithSlackAuth("https://files.slack.com/test.jpg", "xoxb-test-token");
+
+    expect(result).toBe(fileResponse);
+    expect(mockFetch).toHaveBeenCalledTimes(2);
+
+    // First call should have Authorization header and manual redirect
+    expect(mockFetch).toHaveBeenNthCalledWith(1, "https://files.slack.com/test.jpg", {
+      headers: { Authorization: "Bearer xoxb-test-token" },
+      redirect: "manual",
+    });
+
+    // Second call should follow the redirect without Authorization
+    expect(mockFetch).toHaveBeenNthCalledWith(
+      2,
+      "https://cdn.slack-edge.com/presigned-url?sig=abc123",
+      { redirect: "follow" },
+    );
+  });
+
+  it("handles relative redirect URLs", async () => {
+    const { fetchWithSlackAuth } = await import("./media.js");
+
+    // Redirect with relative URL
+    const redirectResponse = new Response(null, {
+      status: 302,
+      headers: { location: "/files/redirect-target" },
+    });
+
+    const fileResponse = new Response(Buffer.from("image data"), {
+      status: 200,
+      headers: { "content-type": "image/jpeg" },
+    });
+
+    mockFetch.mockResolvedValueOnce(redirectResponse).mockResolvedValueOnce(fileResponse);
+
+    await fetchWithSlackAuth("https://files.slack.com/original.jpg", "xoxb-test-token");
+
+    // Second call should resolve the relative URL against the original
+    expect(mockFetch).toHaveBeenNthCalledWith(2, "https://files.slack.com/files/redirect-target", {
+      redirect: "follow",
+    });
+  });
+
+  it("returns redirect response when no location header is provided", async () => {
+    const { fetchWithSlackAuth } = await import("./media.js");
+
+    // Redirect without location header
+    const redirectResponse = new Response(null, {
+      status: 302,
+      // No location header
+    });
+
+    mockFetch.mockResolvedValueOnce(redirectResponse);
+
+    const result = await fetchWithSlackAuth("https://files.slack.com/test.jpg", "xoxb-test-token");
+
+    // Should return the redirect response directly
+    expect(result).toBe(redirectResponse);
+    expect(mockFetch).toHaveBeenCalledTimes(1);
+  });
+
+  it("returns 4xx/5xx responses directly without following", async () => {
+    const { fetchWithSlackAuth } = await import("./media.js");
+
+    const errorResponse = new Response("Not Found", {
+      status: 404,
+    });
+
+    mockFetch.mockResolvedValueOnce(errorResponse);
+
+    const result = await fetchWithSlackAuth("https://files.slack.com/test.jpg", "xoxb-test-token");
+
+    expect(result).toBe(errorResponse);
+    expect(mockFetch).toHaveBeenCalledTimes(1);
+  });
+
+  it("handles 301 permanent redirects", async () => {
+    const { fetchWithSlackAuth } = await import("./media.js");
+
+    const redirectResponse = new Response(null, {
+      status: 301,
+      headers: { location: "https://cdn.slack.com/new-url" },
+    });
+
+    const fileResponse = new Response(Buffer.from("image data"), {
+      status: 200,
+    });
+
+    mockFetch.mockResolvedValueOnce(redirectResponse).mockResolvedValueOnce(fileResponse);
+
+    await fetchWithSlackAuth("https://files.slack.com/test.jpg", "xoxb-test-token");
+
+    expect(mockFetch).toHaveBeenCalledTimes(2);
+    expect(mockFetch).toHaveBeenNthCalledWith(2, "https://cdn.slack.com/new-url", {
+      redirect: "follow",
+    });
+  });
+});
+
+describe("resolveSlackMedia", () => {
+  beforeEach(() => {
+    mockFetch = vi.fn();
+    globalThis.fetch = mockFetch as typeof fetch;
+  });
+
+  afterEach(() => {
+    globalThis.fetch = originalFetch;
+    vi.resetModules();
+  });
+
+  it("prefers url_private_download over url_private", async () => {
+    // Mock the store module
+    vi.doMock("../../media/store.js", () => ({
+      saveMediaBuffer: vi.fn().mockResolvedValue({
+        path: "/tmp/test.jpg",
+        contentType: "image/jpeg",
+      }),
+    }));
+
+    const { resolveSlackMedia } = await import("./media.js");
+
+    const mockResponse = new Response(Buffer.from("image data"), {
+      status: 200,
+      headers: { "content-type": "image/jpeg" },
+    });
+    mockFetch.mockResolvedValueOnce(mockResponse);
+
+    await resolveSlackMedia({
+      files: [
+        {
+          url_private: "https://files.slack.com/private.jpg",
+          url_private_download: "https://files.slack.com/download.jpg",
+          name: "test.jpg",
+        },
+      ],
+      token: "xoxb-test-token",
+      maxBytes: 1024 * 1024,
+    });
+
+    expect(mockFetch).toHaveBeenCalledWith(
+      "https://files.slack.com/download.jpg",
+      expect.anything(),
+    );
+  });
+
+  it("returns null when download fails", async () => {
+    const { resolveSlackMedia } = await import("./media.js");
+
+    // Simulate a network error
+    mockFetch.mockRejectedValueOnce(new Error("Network error"));
+
+    const result = await resolveSlackMedia({
+      files: [{ url_private: "https://files.slack.com/test.jpg", name: "test.jpg" }],
+      token: "xoxb-test-token",
+      maxBytes: 1024 * 1024,
+    });
+
+    expect(result).toBeNull();
+  });
+
+  it("returns null when no files are provided", async () => {
+    const { resolveSlackMedia } = await import("./media.js");
+
+    const result = await resolveSlackMedia({
+      files: [],
+      token: "xoxb-test-token",
+      maxBytes: 1024 * 1024,
+    });
+
+    expect(result).toBeNull();
+  });
+
+  it("skips files without url_private", async () => {
+    const { resolveSlackMedia } = await import("./media.js");
+
+    const result = await resolveSlackMedia({
+      files: [{ name: "test.jpg" }], // No url_private
+      token: "xoxb-test-token",
+      maxBytes: 1024 * 1024,
+    });
+
+    expect(result).toBeNull();
+    expect(mockFetch).not.toHaveBeenCalled();
+  });
+
+  it("falls through to next file when first file returns error", async () => {
+    // Mock the store module
+    vi.doMock("../../media/store.js", () => ({
+      saveMediaBuffer: vi.fn().mockResolvedValue({
+        path: "/tmp/test.jpg",
+        contentType: "image/jpeg",
+      }),
+    }));
+
+    const { resolveSlackMedia } = await import("./media.js");
+
+    // First file: 404
+    const errorResponse = new Response("Not Found", { status: 404 });
+    // Second file: success
+    const successResponse = new Response(Buffer.from("image data"), {
+      status: 200,
+      headers: { "content-type": "image/jpeg" },
+    });
+
+    mockFetch.mockResolvedValueOnce(errorResponse).mockResolvedValueOnce(successResponse);
+
+    const result = await resolveSlackMedia({
+      files: [
+        { url_private: "https://files.slack.com/first.jpg", name: "first.jpg" },
+        { url_private: "https://files.slack.com/second.jpg", name: "second.jpg" },
+      ],
+      token: "xoxb-test-token",
+      maxBytes: 1024 * 1024,
+    });
+
+    expect(result).not.toBeNull();
+    expect(mockFetch).toHaveBeenCalledTimes(2);
+  });
+});

src/slack/monitor/media.ts

@@ -5,6 +5,38 @@ import { fetchRemoteMedia } from "../../media/fetch.js";
 import { saveMediaBuffer } from "../../media/store.js";
 import type { SlackFile } from "../types.js";
 
+/**
+ * Fetches a URL with Authorization header, handling cross-origin redirects.
+ * Node.js fetch strips Authorization headers on cross-origin redirects for security.
+ * Slack's files.slack.com URLs redirect to CDN domains with pre-signed URLs that
+ * don't need the Authorization header, so we handle the initial auth request manually.
+ */
+export async function fetchWithSlackAuth(url: string, token: string): Promise<Response> {
+  // Initial request with auth and manual redirect handling
+  const initialRes = await fetch(url, {
+    headers: { Authorization: `Bearer ${token}` },
+    redirect: "manual",
+  });
+
+  // If not a redirect, return the response directly
+  if (initialRes.status < 300 || initialRes.status >= 400) {
+    return initialRes;
+  }
+
+  // Handle redirect - the redirected URL should be pre-signed and not need auth
+  const redirectUrl = initialRes.headers.get("location");
+  if (!redirectUrl) {
+    return initialRes;
+  }
+
+  // Resolve relative URLs against the original
+  const resolvedUrl = new URL(redirectUrl, url).toString();
+
+  // Follow the redirect without the Authorization header
+  // (Slack's CDN URLs are pre-signed and don't need it)
+  return fetch(resolvedUrl, { redirect: "follow" });
+}
+
 export async function resolveSlackMedia(params: {
   files?: SlackFile[];
   token: string;
@@ -19,10 +51,12 @@ export async function resolveSlackMedia(params: {
     const url = file.url_private_download ?? file.url_private;
     if (!url) continue;
     try {
-      const fetchImpl: FetchLike = (input, init) => {
-        const headers = new Headers(init?.headers);
-        headers.set("Authorization", `Bearer ${params.token}`);
-        return fetch(input, { ...init, headers });
+      // Note: We ignore init options because fetchWithSlackAuth handles
+      // redirect behavior specially. fetchRemoteMedia only passes the URL.
+      const fetchImpl: FetchLike = (input) => {
+        const inputUrl =
+          typeof input === "string" ? input : input instanceof URL ? input.href : input.url;
+        return fetchWithSlackAuth(inputUrl, params.token);
       };
       const fetched = await fetchRemoteMedia({
         url,

src/telegram/bot-native-commands.plugin-auth.test.ts

@@ -0,0 +1,106 @@
+import { describe, expect, it, vi } from "vitest";
+
+import type { ChannelGroupPolicy } from "../config/group-policy.js";
+import type { ClawdbotConfig } from "../config/config.js";
+import type { TelegramAccountConfig } from "../config/types.js";
+import type { RuntimeEnv } from "../runtime.js";
+import { registerTelegramNativeCommands } from "./bot-native-commands.js";
+
+const getPluginCommandSpecs = vi.hoisted(() => vi.fn());
+const matchPluginCommand = vi.hoisted(() => vi.fn());
+const executePluginCommand = vi.hoisted(() => vi.fn());
+
+vi.mock("../plugins/commands.js", () => ({
+  getPluginCommandSpecs,
+  matchPluginCommand,
+  executePluginCommand,
+}));
+
+const deliverReplies = vi.hoisted(() => vi.fn(async () => {}));
+vi.mock("./bot/delivery.js", () => ({ deliverReplies }));
+
+vi.mock("./pairing-store.js", () => ({
+  readTelegramAllowFromStore: vi.fn(async () => []),
+}));
+
+describe("registerTelegramNativeCommands (plugin auth)", () => {
+  it("allows requireAuth:false plugin command even when sender is unauthorized", async () => {
+    const command = {
+      name: "plugin",
+      description: "Plugin command",
+      requireAuth: false,
+      handler: vi.fn(),
+    } as const;
+
+    getPluginCommandSpecs.mockReturnValue([{ name: "plugin", description: "Plugin command" }]);
+    matchPluginCommand.mockReturnValue({ command, args: undefined });
+    executePluginCommand.mockResolvedValue({ text: "ok" });
+
+    const handlers: Record<string, (ctx: unknown) => Promise<void>> = {};
+    const bot = {
+      api: {
+        setMyCommands: vi.fn().mockResolvedValue(undefined),
+        sendMessage: vi.fn(),
+      },
+      command: (name: string, handler: (ctx: unknown) => Promise<void>) => {
+        handlers[name] = handler;
+      },
+    } as const;
+
+    const cfg = {} as ClawdbotConfig;
+    const telegramCfg = {} as TelegramAccountConfig;
+    const resolveGroupPolicy = () =>
+      ({
+        allowlistEnabled: false,
+        allowed: true,
+      }) as ChannelGroupPolicy;
+
+    registerTelegramNativeCommands({
+      bot: bot as unknown as Parameters<typeof registerTelegramNativeCommands>[0]["bot"],
+      cfg,
+      runtime: {} as RuntimeEnv,
+      accountId: "default",
+      telegramCfg,
+      allowFrom: ["999"],
+      groupAllowFrom: [],
+      replyToMode: "off",
+      textLimit: 4000,
+      useAccessGroups: false,
+      nativeEnabled: false,
+      nativeSkillsEnabled: false,
+      nativeDisabledExplicit: false,
+      resolveGroupPolicy,
+      resolveTelegramGroupConfig: () => ({
+        groupConfig: undefined,
+        topicConfig: undefined,
+      }),
+      shouldSkipUpdate: () => false,
+      opts: { token: "token" },
+    });
+
+    const ctx = {
+      message: {
+        chat: { id: 123, type: "private" },
+        from: { id: 111, username: "nope" },
+        message_id: 10,
+        date: 123456,
+      },
+      match: "",
+    };
+
+    await handlers.plugin?.(ctx);
+
+    expect(matchPluginCommand).toHaveBeenCalled();
+    expect(executePluginCommand).toHaveBeenCalledWith(
+      expect.objectContaining({
+        isAuthorizedSender: false,
+      }),
+    );
+    expect(deliverReplies).toHaveBeenCalledWith(
+      expect.objectContaining({
+        replies: [{ text: "ok" }],
+      }),
+    );
+    expect(bot.api.sendMessage).not.toHaveBeenCalled();
+  });
+});

src/telegram/bot-native-commands.ts

@@ -17,9 +17,18 @@ import { dispatchReplyWithBufferedBlockDispatcher } from "../auto-reply/reply/pr
 import { finalizeInboundContext } from "../auto-reply/reply/inbound-context.js";
 import { danger, logVerbose } from "../globals.js";
 import { resolveMarkdownTableMode } from "../config/markdown-tables.js";
+import {
+  normalizeTelegramCommandName,
+  TELEGRAM_COMMAND_NAME_PATTERN,
+} from "../config/telegram-custom-commands.js";
 import { resolveAgentRoute } from "../routing/resolve-route.js";
 import { resolveThreadSessionKeys } from "../routing/session-key.js";
 import { resolveCommandAuthorizedFromAuthorizers } from "../channels/command-gating.js";
+import {
+  executePluginCommand,
+  getPluginCommandSpecs,
+  matchPluginCommand,
+} from "../plugins/commands.js";
 import type { ChannelGroupPolicy } from "../config/group-policy.js";
 import type {
   ReplyToMode,
@@ -42,6 +51,18 @@ import { readTelegramAllowFromStore } from "./pairing-store.js";
 
 type TelegramNativeCommandContext = Context & { match?: string };
 
+type TelegramCommandAuthResult = {
+  chatId: number;
+  isGroup: boolean;
+  isForum: boolean;
+  resolvedThreadId?: number;
+  senderId: string;
+  senderUsername: string;
+  groupConfig?: TelegramGroupConfig;
+  topicConfig?: TelegramTopicConfig;
+  commandAuthorized: boolean;
+};
+
 type RegisterTelegramNativeCommandsParams = {
   bot: Bot;
   cfg: ClawdbotConfig;
@@ -65,6 +86,134 @@ type RegisterTelegramNativeCommandsParams = {
   opts: { token: string };
 };
 
+async function resolveTelegramCommandAuth(params: {
+  msg: NonNullable<TelegramNativeCommandContext["message"]>;
+  bot: Bot;
+  cfg: ClawdbotConfig;
+  telegramCfg: TelegramAccountConfig;
+  allowFrom?: Array<string | number>;
+  groupAllowFrom?: Array<string | number>;
+  useAccessGroups: boolean;
+  resolveGroupPolicy: (chatId: string | number) => ChannelGroupPolicy;
+  resolveTelegramGroupConfig: (
+    chatId: string | number,
+    messageThreadId?: number,
+  ) => { groupConfig?: TelegramGroupConfig; topicConfig?: TelegramTopicConfig };
+  requireAuth: boolean;
+}): Promise<TelegramCommandAuthResult | null> {
+  const {
+    msg,
+    bot,
+    cfg,
+    telegramCfg,
+    allowFrom,
+    groupAllowFrom,
+    useAccessGroups,
+    resolveGroupPolicy,
+    resolveTelegramGroupConfig,
+    requireAuth,
+  } = params;
+  const chatId = msg.chat.id;
+  const isGroup = msg.chat.type === "group" || msg.chat.type === "supergroup";
+  const messageThreadId = (msg as { message_thread_id?: number }).message_thread_id;
+  const isForum = (msg.chat as { is_forum?: boolean }).is_forum === true;
+  const resolvedThreadId = resolveTelegramForumThreadId({
+    isForum,
+    messageThreadId,
+  });
+  const storeAllowFrom = await readTelegramAllowFromStore().catch(() => []);
+  const { groupConfig, topicConfig } = resolveTelegramGroupConfig(chatId, resolvedThreadId);
+  const groupAllowOverride = firstDefined(topicConfig?.allowFrom, groupConfig?.allowFrom);
+  const effectiveGroupAllow = normalizeAllowFromWithStore({
+    allowFrom: groupAllowOverride ?? groupAllowFrom,
+    storeAllowFrom,
+  });
+  const hasGroupAllowOverride = typeof groupAllowOverride !== "undefined";
+  const senderIdRaw = msg.from?.id;
+  const senderId = senderIdRaw ? String(senderIdRaw) : "";
+  const senderUsername = msg.from?.username ?? "";
+
+  if (isGroup && groupConfig?.enabled === false) {
+    await bot.api.sendMessage(chatId, "This group is disabled.");
+    return null;
+  }
+  if (isGroup && topicConfig?.enabled === false) {
+    await bot.api.sendMessage(chatId, "This topic is disabled.");
+    return null;
+  }
+  if (requireAuth && isGroup && hasGroupAllowOverride) {
+    if (
+      senderIdRaw == null ||
+      !isSenderAllowed({
+        allow: effectiveGroupAllow,
+        senderId: String(senderIdRaw),
+        senderUsername,
+      })
+    ) {
+      await bot.api.sendMessage(chatId, "You are not authorized to use this command.");
+      return null;
+    }
+  }
+
+  if (isGroup && useAccessGroups) {
+    const defaultGroupPolicy = cfg.channels?.defaults?.groupPolicy;
+    const groupPolicy = telegramCfg.groupPolicy ?? defaultGroupPolicy ?? "open";
+    if (groupPolicy === "disabled") {
+      await bot.api.sendMessage(chatId, "Telegram group commands are disabled.");
+      return null;
+    }
+    if (groupPolicy === "allowlist" && requireAuth) {
+      if (
+        senderIdRaw == null ||
+        !isSenderAllowed({
+          allow: effectiveGroupAllow,
+          senderId: String(senderIdRaw),
+          senderUsername,
+        })
+      ) {
+        await bot.api.sendMessage(chatId, "You are not authorized to use this command.");
+        return null;
+      }
+    }
+    const groupAllowlist = resolveGroupPolicy(chatId);
+    if (groupAllowlist.allowlistEnabled && !groupAllowlist.allowed) {
+      await bot.api.sendMessage(chatId, "This group is not allowed.");
+      return null;
+    }
+  }
+
+  const dmAllow = normalizeAllowFromWithStore({
+    allowFrom: allowFrom,
+    storeAllowFrom,
+  });
+  const senderAllowed = isSenderAllowed({
+    allow: dmAllow,
+    senderId,
+    senderUsername,
+  });
+  const commandAuthorized = resolveCommandAuthorizedFromAuthorizers({
+    useAccessGroups,
+    authorizers: [{ configured: dmAllow.hasEntries, allowed: senderAllowed }],
+    modeWhenAccessGroupsOff: "configured",
+  });
+  if (requireAuth && !commandAuthorized) {
+    await bot.api.sendMessage(chatId, "You are not authorized to use this command.");
+    return null;
+  }
+
+  return {
+    chatId,
+    isGroup,
+    isForum,
+    resolvedThreadId,
+    senderId,
+    senderUsername,
+    groupConfig,
+    topicConfig,
+    commandAuthorized,
+  };
+}
+
 export const registerTelegramNativeCommands = ({
   bot,
   cfg,
@@ -103,11 +252,50 @@ export const registerTelegramNativeCommands = ({
     runtime.error?.(danger(issue.message));
   }
   const customCommands = customResolution.commands;
+  const pluginCommandSpecs = getPluginCommandSpecs();
+  const pluginCommands: Array<{ command: string; description: string }> = [];
+  const existingCommands = new Set(
+    [
+      ...nativeCommands.map((command) => command.name),
+      ...customCommands.map((command) => command.command),
+    ].map((command) => command.toLowerCase()),
+  );
+  const pluginCommandNames = new Set<string>();
+  for (const spec of pluginCommandSpecs) {
+    const normalized = normalizeTelegramCommandName(spec.name);
+    if (!normalized || !TELEGRAM_COMMAND_NAME_PATTERN.test(normalized)) {
+      runtime.error?.(
+        danger(
+          `Plugin command "/${spec.name}" is invalid for Telegram (use a-z, 0-9, underscore; max 32 chars).`,
+        ),
+      );
+      continue;
+    }
+    const description = spec.description.trim();
+    if (!description) {
+      runtime.error?.(danger(`Plugin command "/${normalized}" is missing a description.`));
+      continue;
+    }
+    if (existingCommands.has(normalized)) {
+      runtime.error?.(
+        danger(`Plugin command "/${normalized}" conflicts with an existing Telegram command.`),
+      );
+      continue;
+    }
+    if (pluginCommandNames.has(normalized)) {
+      runtime.error?.(danger(`Plugin command "/${normalized}" is duplicated.`));
+      continue;
+    }
+    pluginCommandNames.add(normalized);
+    existingCommands.add(normalized);
+    pluginCommands.push({ command: normalized, description });
+  }
   const allCommands: Array<{ command: string; description: string }> = [
     ...nativeCommands.map((command) => ({
       command: command.name,
       description: command.description,
     })),
+    ...pluginCommands,
     ...customCommands,
   ];
 
@@ -124,99 +312,30 @@ export const registerTelegramNativeCommands = ({
           const msg = ctx.message;
           if (!msg) return;
           if (shouldSkipUpdate(ctx)) return;
-          const chatId = msg.chat.id;
-          const isGroup = msg.chat.type === "group" || msg.chat.type === "supergroup";
-          const messageThreadId = (msg as { message_thread_id?: number }).message_thread_id;
-          const isForum = (msg.chat as { is_forum?: boolean }).is_forum === true;
-          const resolvedThreadId = resolveTelegramForumThreadId({
+          const auth = await resolveTelegramCommandAuth({
+            msg,
+            bot,
+            cfg,
+            telegramCfg,
+            allowFrom,
+            groupAllowFrom,
+            useAccessGroups,
+            resolveGroupPolicy,
+            resolveTelegramGroupConfig,
+            requireAuth: true,
+          });
+          if (!auth) return;
+          const {
+            chatId,
+            isGroup,
             isForum,
-            messageThreadId,
-          });
-          const storeAllowFrom = await readTelegramAllowFromStore().catch(() => []);
-          const { groupConfig, topicConfig } = resolveTelegramGroupConfig(chatId, resolvedThreadId);
-          const groupAllowOverride = firstDefined(topicConfig?.allowFrom, groupConfig?.allowFrom);
-          const effectiveGroupAllow = normalizeAllowFromWithStore({
-            allowFrom: groupAllowOverride ?? groupAllowFrom,
-            storeAllowFrom,
-          });
-          const hasGroupAllowOverride = typeof groupAllowOverride !== "undefined";
-
-          if (isGroup && groupConfig?.enabled === false) {
-            await bot.api.sendMessage(chatId, "This group is disabled.");
-            return;
-          }
-          if (isGroup && topicConfig?.enabled === false) {
-            await bot.api.sendMessage(chatId, "This topic is disabled.");
-            return;
-          }
-          if (isGroup && hasGroupAllowOverride) {
-            const senderId = msg.from?.id;
-            const senderUsername = msg.from?.username ?? "";
-            if (
-              senderId == null ||
-              !isSenderAllowed({
-                allow: effectiveGroupAllow,
-                senderId: String(senderId),
-                senderUsername,
-              })
-            ) {
-              await bot.api.sendMessage(chatId, "You are not authorized to use this command.");
-              return;
-            }
-          }
-
-          if (isGroup && useAccessGroups) {
-            const defaultGroupPolicy = cfg.channels?.defaults?.groupPolicy;
-            const groupPolicy = telegramCfg.groupPolicy ?? defaultGroupPolicy ?? "open";
-            if (groupPolicy === "disabled") {
-              await bot.api.sendMessage(chatId, "Telegram group commands are disabled.");
-              return;
-            }
-            if (groupPolicy === "allowlist") {
-              const senderId = msg.from?.id;
-              if (senderId == null) {
-                await bot.api.sendMessage(chatId, "You are not authorized to use this command.");
-                return;
-              }
-              const senderUsername = msg.from?.username ?? "";
-              if (
-                !isSenderAllowed({
-                  allow: effectiveGroupAllow,
-                  senderId: String(senderId),
-                  senderUsername,
-                })
-              ) {
-                await bot.api.sendMessage(chatId, "You are not authorized to use this command.");
-                return;
-              }
-            }
-            const groupAllowlist = resolveGroupPolicy(chatId);
-            if (groupAllowlist.allowlistEnabled && !groupAllowlist.allowed) {
-              await bot.api.sendMessage(chatId, "This group is not allowed.");
-              return;
-            }
-          }
-
-          const senderId = msg.from?.id ? String(msg.from.id) : "";
-          const senderUsername = msg.from?.username ?? "";
-          const dmAllow = normalizeAllowFromWithStore({
-            allowFrom: allowFrom,
-            storeAllowFrom,
-          });
-          const senderAllowed = isSenderAllowed({
-            allow: dmAllow,
+            resolvedThreadId,
             senderId,
             senderUsername,
-          });
-          const commandAuthorized = resolveCommandAuthorizedFromAuthorizers({
-            useAccessGroups,
-            authorizers: [{ configured: dmAllow.hasEntries, allowed: senderAllowed }],
-            modeWhenAccessGroupsOff: "configured",
-          });
-          if (!commandAuthorized) {
-            await bot.api.sendMessage(chatId, "You are not authorized to use this command.");
-            return;
-          }
+            groupConfig,
+            topicConfig,
+            commandAuthorized,
+          } = auth;
 
           const commandDefinition = findCommandByNativeName(command.name, "telegram");
           const rawText = ctx.match?.trim() ?? "";
@@ -362,6 +481,66 @@ export const registerTelegramNativeCommands = ({
           });
         });
       }
+
+      for (const pluginCommand of pluginCommands) {
+        bot.command(pluginCommand.command, async (ctx: TelegramNativeCommandContext) => {
+          const msg = ctx.message;
+          if (!msg) return;
+          if (shouldSkipUpdate(ctx)) return;
+          const chatId = msg.chat.id;
+          const rawText = ctx.match?.trim() ?? "";
+          const commandBody = `/${pluginCommand.command}${rawText ? ` ${rawText}` : ""}`;
+          const match = matchPluginCommand(commandBody);
+          if (!match) {
+            await bot.api.sendMessage(chatId, "Command not found.");
+            return;
+          }
+          const auth = await resolveTelegramCommandAuth({
+            msg,
+            bot,
+            cfg,
+            telegramCfg,
+            allowFrom,
+            groupAllowFrom,
+            useAccessGroups,
+            resolveGroupPolicy,
+            resolveTelegramGroupConfig,
+            requireAuth: match.command.requireAuth !== false,
+          });
+          if (!auth) return;
+          const { resolvedThreadId, senderId, commandAuthorized } = auth;
+
+          const result = await executePluginCommand({
+            command: match.command,
+            args: match.args,
+            senderId,
+            channel: "telegram",
+            isAuthorizedSender: commandAuthorized,
+            commandBody,
+            config: cfg,
+          });
+          const tableMode = resolveMarkdownTableMode({
+            cfg,
+            channel: "telegram",
+            accountId,
+          });
+          const chunkMode = resolveChunkMode(cfg, "telegram", accountId);
+
+          await deliverReplies({
+            replies: [result],
+            chatId: String(chatId),
+            token: opts.token,
+            runtime,
+            bot,
+            replyToMode,
+            textLimit,
+            messageThreadId: resolvedThreadId,
+            tableMode,
+            chunkMode,
+            linkPreview: telegramCfg.linkPreview,
+          });
+        });
+      }
     }
   } else if (nativeDisabledExplicit) {
     bot.api.setMyCommands([]).catch((err) => {

src/telegram/bot/delivery.ts

@@ -17,6 +17,7 @@ import { isGifMedia } from "../../media/mime.js";
 import { saveMediaBuffer } from "../../media/store.js";
 import type { RuntimeEnv } from "../../runtime.js";
 import { loadWebMedia } from "../../web/media.js";
+import { buildInlineKeyboard } from "../send.js";
 import { resolveTelegramVoiceSend } from "../voice.js";
 import { buildTelegramThreadParams, resolveTelegramReplyId } from "./helpers.js";
 import type { TelegramContext } from "./types.js";
@@ -80,9 +81,17 @@ export async function deliverReplies(params: {
       : reply.mediaUrl
         ? [reply.mediaUrl]
         : [];
+    const telegramData = reply.channelData?.telegram as
+      | { buttons?: Array<Array<{ text: string; callback_data: string }>> }
+      | undefined;
+    const replyMarkup = buildInlineKeyboard(telegramData?.buttons);
     if (mediaList.length === 0) {
       const chunks = chunkText(reply.text || "");
-      for (const chunk of chunks) {
+      for (let i = 0; i < chunks.length; i += 1) {
+        const chunk = chunks[i];
+        if (!chunk) continue;
+        // Only attach buttons to the first chunk.
+        const shouldAttachButtons = i === 0 && replyMarkup;
         await sendTelegramText(bot, chatId, chunk.html, runtime, {
           replyToMessageId:
             replyToId && (replyToMode === "all" || !hasReplied) ? replyToId : undefined,
@@ -90,6 +99,7 @@ export async function deliverReplies(params: {
           textMode: "html",
           plainText: chunk.text,
           linkPreview,
+          replyMarkup: shouldAttachButtons ? replyMarkup : undefined,
         });
         if (replyToId && !hasReplied) {
           hasReplied = true;
@@ -125,10 +135,12 @@ export async function deliverReplies(params: {
       first = false;
       const replyToMessageId =
         replyToId && (replyToMode === "all" || !hasReplied) ? replyToId : undefined;
+      const shouldAttachButtonsToMedia = isFirstMedia && replyMarkup && !followUpText;
       const mediaParams: Record<string, unknown> = {
         caption: htmlCaption,
         reply_to_message_id: replyToMessageId,
         ...(htmlCaption ? { parse_mode: "HTML" } : {}),
+        ...(shouldAttachButtonsToMedia ? { reply_markup: replyMarkup } : {}),
       };
       if (threadParams) {
         mediaParams.message_thread_id = threadParams.message_thread_id;
@@ -183,6 +195,7 @@ export async function deliverReplies(params: {
                 hasReplied,
                 messageThreadId,
                 linkPreview,
+                replyMarkup,
               });
               // Skip this media item; continue with next.
               continue;
@@ -207,7 +220,8 @@ export async function deliverReplies(params: {
       // Chunk it in case it's extremely long (same logic as text-only replies).
       if (pendingFollowUpText && isFirstMedia) {
         const chunks = chunkText(pendingFollowUpText);
-        for (const chunk of chunks) {
+        for (let i = 0; i < chunks.length; i += 1) {
+          const chunk = chunks[i];
           const replyToMessageIdFollowup =
             replyToId && (replyToMode === "all" || !hasReplied) ? replyToId : undefined;
           await sendTelegramText(bot, chatId, chunk.html, runtime, {
@@ -216,6 +230,7 @@ export async function deliverReplies(params: {
             textMode: "html",
             plainText: chunk.text,
             linkPreview,
+            replyMarkup: i === 0 ? replyMarkup : undefined,
           });
           if (replyToId && !hasReplied) {
             hasReplied = true;
@@ -277,10 +292,12 @@ async function sendTelegramVoiceFallbackText(opts: {
   hasReplied: boolean;
   messageThreadId?: number;
   linkPreview?: boolean;
+  replyMarkup?: ReturnType<typeof buildInlineKeyboard>;
 }): Promise<boolean> {
   const chunks = opts.chunkText(opts.text);
   let hasReplied = opts.hasReplied;
-  for (const chunk of chunks) {
+  for (let i = 0; i < chunks.length; i += 1) {
+    const chunk = chunks[i];
     await sendTelegramText(opts.bot, opts.chatId, chunk.html, opts.runtime, {
       replyToMessageId:
         opts.replyToId && (opts.replyToMode === "all" || !hasReplied) ? opts.replyToId : undefined,
@@ -288,6 +305,7 @@ async function sendTelegramVoiceFallbackText(opts: {
       textMode: "html",
       plainText: chunk.text,
       linkPreview: opts.linkPreview,
+      replyMarkup: i === 0 ? opts.replyMarkup : undefined,
     });
     if (opts.replyToId && !hasReplied) {
       hasReplied = true;
@@ -322,6 +340,7 @@ async function sendTelegramText(
     textMode?: "markdown" | "html";
     plainText?: string;
     linkPreview?: boolean;
+    replyMarkup?: ReturnType<typeof buildInlineKeyboard>;
   },
 ): Promise<number | undefined> {
   const baseParams = buildTelegramSendParams({
@@ -337,6 +356,7 @@ async function sendTelegramText(
     const res = await bot.api.sendMessage(chatId, htmlText, {
       parse_mode: "HTML",
       ...(linkPreviewOptions ? { link_preview_options: linkPreviewOptions } : {}),
+      ...(opts?.replyMarkup ? { reply_markup: opts.replyMarkup } : {}),
       ...baseParams,
     });
     return res.message_id;
@@ -347,6 +367,7 @@ async function sendTelegramText(
       const fallbackText = opts?.plainText ?? text;
       const res = await bot.api.sendMessage(chatId, fallbackText, {
         ...(linkPreviewOptions ? { link_preview_options: linkPreviewOptions } : {}),
+        ...(opts?.replyMarkup ? { reply_markup: opts.replyMarkup } : {}),
         ...baseParams,
       });
       return res.message_id;

src/wizard/onboarding.gateway-config.ts

@@ -93,11 +93,6 @@ export async function configureGatewayForOnboarding(
       : ((await prompter.select({
           message: "Gateway auth",
           options: [
-            {
-              value: "off",
-              label: "Off (loopback only)",
-              hint: "Not recommended unless you fully trust local processes",
-            },
             {
               value: "token",
               label: "Token",
@@ -165,7 +160,6 @@ export async function configureGatewayForOnboarding(
 
   // Safety + constraints:
   // - Tailscale wants bind=loopback so we never expose a non-loopback server + tailscale serve/funnel at once.
-  // - Auth off only allowed for bind=loopback.
   // - Funnel requires password auth.
   if (tailscaleMode !== "off" && bind !== "loopback") {
     await prompter.note("Tailscale requires bind=loopback. Adjusting bind to loopback.", "Note");
@@ -173,11 +167,6 @@ export async function configureGatewayForOnboarding(
     customBindHost = undefined;
   }
 
-  if (authMode === "off" && bind !== "loopback") {
-    await prompter.note("Non-loopback bind requires auth. Switching to token auth.", "Note");
-    authMode = "token";
-  }
-
   if (tailscaleMode === "funnel" && authMode !== "password") {
     await prompter.note("Tailscale funnel requires password auth.", "Note");
     authMode = "password";

src/wizard/onboarding.ts

@@ -51,12 +51,26 @@ async function requireRiskAcknowledgement(params: {
 
   await params.prompter.note(
     [
-      "Please read: https://docs.clawd.bot/security",
+      "Security warning — please read.",
       "",
-      "Clawdbot agents can run commands, read/write files, and act through any tools you enable. They can only send messages on channels you configure (for example, an account you log in on this machine, or a bot account like Slack/Discord).",
+      "Clawdbot is a hobby project and still in beta. Expect sharp edges.",
+      "This bot can read files and run actions if tools are enabled.",
+      "A bad prompt can trick it into doing unsafe things.",
       "",
-      "If you’re new to this, start with the sandbox and least privilege. It helps limit what an agent can do if it’s tricked or makes a mistake.",
-      "Learn more: https://docs.clawd.bot/sandboxing",
+      "If you’re not comfortable with basic security and access control, don’t run Clawdbot.",
+      "Ask someone experienced to help before enabling tools or exposing it to the internet.",
+      "",
+      "Recommended baseline:",
+      "- Pairing/allowlists + mention gating.",
+      "- Sandbox + least-privilege tools.",
+      "- Keep secrets out of the agent’s reachable filesystem.",
+      "- Use the strongest available model for any bot with tools or untrusted inboxes.",
+      "",
+      "Run regularly:",
+      "clawdbot security audit --deep",
+      "clawdbot security audit --fix",
+      "",
+      "Must read: https://docs.clawd.bot/gateway/security",
     ].join("\n"),
     "Security",
   );
@@ -230,7 +244,6 @@ export async function runOnboardingWizard(
       return "Auto";
     };
     const formatAuth = (value: GatewayAuthChoice) => {
-      if (value === "off") return "Off (loopback only)";
       if (value === "token") return "Token (default)";
       return "Password";
     };