diff --git a/.env.example b/.env.example
new file mode 100644
index 000000000..29652fe46
--- /dev/null
+++ b/.env.example
@@ -0,0 +1,5 @@
+# Copy to .env and fill with your Twilio credentials
+TWILIO_ACCOUNT_SID=ACxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx
+TWILIO_AUTH_TOKEN=your_auth_token_here
+# Must be a WhatsApp-enabled Twilio number, prefixed with whatsapp:
+TWILIO_WHATSAPP_FROM=whatsapp:+17343367101
diff --git a/.gitignore b/.gitignore
new file mode 100644
index 000000000..885509ebd
--- /dev/null
+++ b/.gitignore
@@ -0,0 +1,4 @@
+node_modules
+.env
+dist
+pnpm-lock.yaml
diff --git a/README.md b/README.md
new file mode 100644
index 000000000..5c43d92b9
--- /dev/null
+++ b/README.md
@@ -0,0 +1,55 @@
+# Warelay — WhatsApp Relay CLI (Twilio)
+
+Small TypeScript CLI to send, monitor, and webhook WhatsApp messages via Twilio. Supports Tailscale Funnel and config-driven auto-replies.
+
+## Setup
+
+1. `pnpm install`
+2. Copy `.env.example` to `.env` and fill in `TWILIO_ACCOUNT_SID`, `TWILIO_AUTH_TOKEN`, and `TWILIO_WHATSAPP_FROM` (use your approved WhatsApp-enabled Twilio number, prefixed with `whatsapp:`).
+   - Alternatively, use API keys: `TWILIO_API_KEY` + `TWILIO_API_SECRET` instead of `TWILIO_AUTH_TOKEN`.
+3. Build once for the runnable bin: `pnpm build`
+
+## Commands
+
+- Send: `pnpm warelay send --to +15551234567 --message "Hello" --wait 20 --poll 2`
+  - `--wait` seconds (default 20) waits for a terminal delivery status; exits non-zero on failed/undelivered/canceled.
+  - `--poll` seconds (default 2) sets the polling interval while waiting.
+- Monitor (polling): `pnpm warelay monitor` (defaults: 5s interval, 5m lookback)
+  - Options: `--interval <seconds>`, `--lookback <minutes>`
+- Webhook (push, works well with Tailscale): `pnpm warelay webhook --port 42873 --reply "Got it!"`
+  - Points Twilio’s “Incoming Message” webhook to `http://<your-host>:42873/webhook/whatsapp`
+  - With Tailscale, expose it: `tailscale serve tcp 42873 127.0.0.1:42873` and use your tailnet IP.
+  - Customize path if desired: `--path /hooks/wa`
+  - If no `--reply`, auto-reply can be configured via `~/.warelay/warelay.json` (JSON5)
+- Setup helper: `pnpm warelay setup --port 42873 --path /webhook/whatsapp`
+  - Validates Twilio env, confirms `tailscale` binary, starts the webhook, enables Tailscale Funnel, and sets the Twilio incoming webhook to your Funnel URL.
+
+## Config-driven auto-replies
+
+Put a JSON5 config at `~/.warelay/warelay.json`. Examples:
+
+```json5
+{
+  inbound: {
+    // Static text reply with templating
+    reply: { mode: 'text', text: 'Echo: {{Body}}' }
+  }
+}
+
+// Command-based reply (stdout becomes the reply)
+{
+  inbound: {
+    reply: {
+      mode: 'command',
+      command: ['bash', '-lc', 'echo "You said: {{Body}} from {{From}}"']
+    }
+  }
+}
+```
+
+During dev you can run without building: `pnpm dev -- <subcommand>` (e.g. `pnpm dev -- send --to +1...`).
+
+## Notes
+
+- Monitor uses polling; webhook mode is push (recommended).
+- Stop monitor/webhook with `Ctrl+C`.
diff --git a/package.json b/package.json
new file mode 100644
index 000000000..a3ca9348e
--- /dev/null
+++ b/package.json
@@ -0,0 +1,43 @@
+{
+  "name": "warelay",
+  "version": "1.0.0",
+  "description": "WhatsApp relay CLI (send, monitor, webhook, auto-reply) using Twilio",
+  "type": "module",
+  "main": "dist/index.js",
+  "bin": {
+    "warelay": "dist/index.js",
+    "warely": "dist/index.js"
+  },
+  "scripts": {
+    "dev": "tsx src/index.ts",
+    "build": "tsc -p tsconfig.json",
+    "start": "node dist/index.js",
+    "warelay": "node dist/index.js",
+    "warely": "node dist/index.js",
+    "lint": "echo \"No linter configured\"",
+    "test": "echo \"No tests yet\""
+  },
+  "keywords": [],
+  "author": "",
+  "license": "MIT",
+  "engines": {
+    "node": ">=22.0.0"
+  },
+  "packageManager": "pnpm@10.23.0",
+  "dependencies": {
+    "body-parser": "^2.2.0",
+    "commander": "^14.0.2",
+    "dotenv": "^17.2.3",
+    "express": "^5.1.0",
+    "json5": "^2.2.3",
+    "twilio": "^5.10.6"
+  },
+  "devDependencies": {
+    "@types/body-parser": "^1.19.6",
+    "@types/express": "^5.0.5",
+    "@types/json5": "^2.2.0",
+    "@types/node": "^24.10.1",
+    "tsx": "^4.20.6",
+    "typescript": "^5.9.3"
+  }
+}
diff --git a/src/index.ts b/src/index.ts
new file mode 100644
index 000000000..48c8aa11a
--- /dev/null
+++ b/src/index.ts
@@ -0,0 +1,511 @@
+#!/usr/bin/env node
+import { Command } from 'commander';
+import dotenv from 'dotenv';
+import process from 'node:process';
+import Twilio from 'twilio';
+import type { MessageInstance } from 'twilio/lib/rest/api/v2010/account/message.js';
+import express from 'express';
+import bodyParser from 'body-parser';
+import { execFile } from 'node:child_process';
+import { promisify } from 'node:util';
+import fs from 'node:fs';
+import path from 'node:path';
+import os from 'node:os';
+import JSON5 from 'json5';
+
+dotenv.config();
+
+const program = new Command();
+
+type AuthMode =
+  | { accountSid: string; authToken: string }
+  | { accountSid: string; apiKey: string; apiSecret: string };
+
+type EnvConfig = {
+  accountSid: string;
+  whatsappFrom: string;
+  auth: AuthMode;
+};
+
+function readEnv(): EnvConfig {
+  const accountSid = process.env.TWILIO_ACCOUNT_SID;
+  const whatsappFrom = process.env.TWILIO_WHATSAPP_FROM;
+  const authToken = process.env.TWILIO_AUTH_TOKEN;
+  const apiKey = process.env.TWILIO_API_KEY;
+  const apiSecret = process.env.TWILIO_API_SECRET;
+
+  if (!accountSid) {
+    console.error('Missing env var TWILIO_ACCOUNT_SID');
+    process.exit(1);
+  }
+  if (!whatsappFrom) {
+    console.error('Missing env var TWILIO_WHATSAPP_FROM');
+    process.exit(1);
+  }
+
+  let auth: AuthMode | undefined;
+  if (apiKey && apiSecret) {
+    auth = { accountSid, apiKey, apiSecret };
+  } else if (authToken) {
+    auth = { accountSid, authToken };
+  } else {
+    console.error('Provide either TWILIO_AUTH_TOKEN or (TWILIO_API_KEY and TWILIO_API_SECRET)');
+    process.exit(1);
+  }
+
+  return {
+    accountSid,
+    whatsappFrom,
+    auth
+  };
+}
+
+const execFileAsync = promisify(execFile);
+
+async function ensureBinary(name: string) {
+  try {
+    await execFileAsync('which', [name]);
+  } catch {
+    console.error(`Missing required binary: ${name}. Please install it.`);
+    process.exit(1);
+  }
+}
+
+function withWhatsAppPrefix(number: string): string {
+  return number.startsWith('whatsapp:') ? number : `whatsapp:${number}`;
+}
+
+const CONFIG_PATH = path.join(os.homedir(), '.warelay', 'warelay.json');
+
+type ReplyMode = 'text' | 'command';
+
+type WarelayConfig = {
+  inbound?: {
+    reply?: {
+      mode: ReplyMode;
+      text?: string; // for mode=text, can contain {{Body}}
+      command?: string[]; // for mode=command, argv with templates
+      template?: string; // prepend template string when building command/prompt
+    };
+  };
+};
+
+function loadConfig(): WarelayConfig {
+  try {
+    if (!fs.existsSync(CONFIG_PATH)) return {};
+    const raw = fs.readFileSync(CONFIG_PATH, 'utf-8');
+    return JSON5.parse(raw) as WarelayConfig;
+  } catch (err) {
+    console.error(`Failed to read config at ${CONFIG_PATH}`, err);
+    return {};
+  }
+}
+
+type MsgContext = {
+  Body?: string;
+  From?: string;
+  To?: string;
+  MessageSid?: string;
+};
+
+function applyTemplate(str: string, ctx: MsgContext) {
+  return str.replace(/{{\s*(\w+)\s*}}/g, (_, key) => {
+    const value = (ctx as Record<string, unknown>)[key];
+    return value == null ? '' : String(value);
+  });
+}
+
+async function getReplyFromConfig(ctx: MsgContext): Promise<string | undefined> {
+  const cfg = loadConfig();
+  const reply = cfg.inbound?.reply;
+  if (!reply) return undefined;
+
+  if (reply.mode === 'text' && reply.text) {
+    return applyTemplate(reply.text, ctx);
+  }
+
+  if (reply.mode === 'command' && reply.command?.length) {
+    const argv = reply.command.map((part) => applyTemplate(part, ctx));
+    const templatePrefix = reply.template ? applyTemplate(reply.template, ctx) : '';
+    const finalArgv = templatePrefix ? [argv[0], templatePrefix, ...argv.slice(1)] : argv;
+    try {
+      const { stdout } = await execFileAsync(finalArgv[0], finalArgv.slice(1), {
+        maxBuffer: 1024 * 1024
+      });
+      return stdout.trim();
+    } catch (err) {
+      console.error('Command auto-reply failed', err);
+      return undefined;
+    }
+  }
+
+  return undefined;
+}
+
+function createClient(env: EnvConfig) {
+  if ('authToken' in env.auth) {
+    return Twilio(env.accountSid, env.auth.authToken, {
+      accountSid: env.accountSid
+    });
+  }
+  return Twilio(env.auth.apiKey, env.auth.apiSecret, {
+    accountSid: env.accountSid
+  });
+}
+
+async function sendMessage(to: string, body: string) {
+  const env = readEnv();
+  const client = createClient(env);
+  const from = withWhatsAppPrefix(env.whatsappFrom);
+  const toNumber = withWhatsAppPrefix(to);
+
+  try {
+    const message = await client.messages.create({
+      from,
+      to: toNumber,
+      body
+    });
+
+    console.log(`✅ Request accepted. Message SID: ${message.sid} -> ${toNumber}`);
+    return { client, sid: message.sid };
+  } catch (err) {
+    const anyErr = err as Record<string, unknown>;
+    const code = anyErr?.['code'];
+    const msg = anyErr?.['message'];
+    const more = anyErr?.['moreInfo'];
+    const status = anyErr?.['status'];
+    console.error(
+      `❌ Twilio send failed${code ? ` (code ${code})` : ''}${status ? ` status ${status}` : ''}: ${msg ?? err}`
+    );
+    if (more) console.error(`More info: ${more}`);
+    // Some Twilio errors include response.body with more context.
+    const responseBody = (anyErr?.['response'] as Record<string, unknown> | undefined)?.['body'];
+    if (responseBody) {
+      console.error('Response body:', JSON.stringify(responseBody, null, 2));
+    }
+    process.exit(1);
+  }
+}
+
+const successTerminalStatuses = new Set(['delivered', 'read']);
+const failureTerminalStatuses = new Set(['failed', 'undelivered', 'canceled']);
+
+async function waitForFinalStatus(
+  client: ReturnType<typeof createClient>,
+  sid: string,
+  timeoutSeconds: number,
+  pollSeconds: number
+) {
+  const deadline = Date.now() + timeoutSeconds * 1000;
+  while (Date.now() < deadline) {
+    const m = await client.messages(sid).fetch();
+    const status = m.status ?? 'unknown';
+    if (successTerminalStatuses.has(status)) {
+      console.log(`✅ Delivered (status: ${status})`);
+      return;
+    }
+    if (failureTerminalStatuses.has(status)) {
+      console.error(
+        `❌ Delivery failed (status: ${status}${
+          m.errorCode ? `, code ${m.errorCode}` : ''
+        })${m.errorMessage ? `: ${m.errorMessage}` : ''}`
+      );
+      process.exit(1);
+    }
+    await sleep(pollSeconds * 1000);
+  }
+  console.log('ℹ️  Timed out waiting for final status; message may still be in flight.');
+}
+
+async function startWebhook(
+  port: number,
+  path = '/webhook/whatsapp',
+  autoReply?: string
+) {
+  const env = readEnv();
+  const app = express();
+
+  // Twilio sends application/x-www-form-urlencoded
+  app.use(bodyParser.urlencoded({ extended: false }));
+
+  app.post(path, async (req, res) => {
+    const { From, To, Body, MessageSid } = req.body ?? {};
+    console.log(`[INBOUND] ${From} -> ${To} (${MessageSid}): ${Body}`);
+
+    let replyText = autoReply;
+    if (!replyText) {
+      replyText = await getReplyFromConfig({
+        Body,
+        From,
+        To,
+        MessageSid
+      });
+    }
+
+    if (replyText) {
+      try {
+        const client = createClient(env);
+        await client.messages.create({
+          from: To,
+          to: From,
+          body: replyText
+        });
+        console.log(`↩️  Auto-replied to ${From}`);
+      } catch (err) {
+        console.error('Failed to auto-reply', err);
+      }
+    }
+
+    // Respond 200 OK to Twilio
+    res.type('text/xml').send('<Response></Response>');
+  });
+
+  return new Promise<void>((resolve) => {
+    app.listen(port, () => {
+      console.log(`📥 Webhook listening on http://localhost:${port}${path}`);
+      resolve();
+    });
+  });
+}
+
+async function getTailnetHostname() {
+  const { stdout } = await execFileAsync('tailscale', ['status', '--json'], { maxBuffer: 2_000_000 });
+  const parsed = JSON.parse(stdout);
+  const dns = parsed?.Self?.DNSName as string | undefined;
+  const ips = parsed?.Self?.TailscaleIPs as string[] | undefined;
+  if (dns && dns.length > 0) return dns.replace(/\.$/, '');
+  if (ips && ips.length > 0) return ips[0];
+  throw new Error('Could not determine Tailscale DNS or IP');
+}
+
+async function ensureFunnel(port: number) {
+  try {
+    const { stdout } = await execFileAsync('tailscale', ['funnel', `${port}`, `127.0.0.1:${port}`], {
+      maxBuffer: 200_000
+    });
+    console.log(stdout.trim());
+  } catch (err) {
+    console.error('Failed to enable Tailscale Funnel. Is it allowed on your tailnet?', err);
+    process.exit(1);
+  }
+}
+
+async function findWhatsappSenderSid(client: ReturnType<typeof createClient>, from: string) {
+  const resp = await (client as any).request({
+    method: 'get',
+    uri: 'https://messaging.twilio.com/v2/Channels/Senders',
+    qs: { Channel: 'whatsapp', PageSize: 50 }
+  });
+  const senders = resp?.data?.senders as Array<any>;
+  if (!Array.isArray(senders)) {
+    throw new Error('Unable to list WhatsApp senders');
+  }
+  const match = senders.find((s) => s.sender_id === withWhatsAppPrefix(from));
+  if (!match) {
+    throw new Error(`Could not find sender ${withWhatsAppPrefix(from)} in Twilio account`);
+  }
+  return match.sid as string;
+}
+
+async function updateWebhook(
+  client: ReturnType<typeof createClient>,
+  senderSid: string,
+  url: string,
+  method: 'POST' | 'GET' = 'POST'
+) {
+  await (client as any).request({
+    method: 'post',
+    uri: `https://messaging.twilio.com/v2/Channels/Senders/${senderSid}`,
+    form: {
+      CallbackUrl: url,
+      CallbackMethod: method
+    }
+  });
+  console.log(`✅ Twilio webhook set to ${url}`);
+}
+
+function sleep(ms: number) {
+  return new Promise((resolve) => setTimeout(resolve, ms));
+}
+
+async function monitor(intervalSeconds: number, lookbackMinutes: number) {
+  const env = readEnv();
+  const client = createClient(env);
+  const from = withWhatsAppPrefix(env.whatsappFrom);
+
+  let since = new Date(Date.now() - lookbackMinutes * 60_000);
+  const seen = new Set<string>();
+
+  console.log(
+    `📡 Monitoring inbound messages to ${from} (poll ${intervalSeconds}s, lookback ${lookbackMinutes}m)`
+  );
+
+  const updateSince = (date?: Date | null) => {
+    if (!date) return;
+    if (date.getTime() > since.getTime()) {
+      since = date;
+    }
+  };
+
+  let keepRunning = true;
+  process.on('SIGINT', () => {
+    keepRunning = false;
+    console.log('\n👋 Stopping monitor');
+  });
+
+  while (keepRunning) {
+    try {
+      const messages = await client.messages.list({
+        to: from,
+        dateSentAfter: since,
+        limit: 50
+      });
+
+      messages
+        .filter((m: MessageInstance) => m.direction === 'inbound')
+        .sort((a: MessageInstance, b: MessageInstance) => {
+          const da = a.dateCreated?.getTime() ?? 0;
+          const db = b.dateCreated?.getTime() ?? 0;
+          return da - db;
+        })
+        .forEach((m: MessageInstance) => {
+          if (seen.has(m.sid)) return;
+          seen.add(m.sid);
+          const time = m.dateCreated?.toISOString() ?? 'unknown time';
+          const fromNum = m.from ?? 'unknown sender';
+          console.log(`\n[${time}] ${fromNum} -> ${m.to}: ${m.body ?? ''}`);
+          updateSince(m.dateCreated);
+        });
+    } catch (err) {
+      console.error('Error while polling messages', err);
+    }
+
+    await sleep(intervalSeconds * 1000);
+  }
+}
+
+program.name('warelay').description('WhatsApp relay CLI using Twilio').version('1.0.0');
+
+program
+  .command('send')
+  .description('Send a WhatsApp message')
+  .requiredOption('-t, --to <number>', 'Recipient number in E.164 (e.g. +15551234567)')
+  .requiredOption('-m, --message <text>', 'Message body')
+  .option('-w, --wait <seconds>', 'Wait for delivery status (0 to skip)', '20')
+  .option('-p, --poll <seconds>', 'Polling interval while waiting', '2')
+  .addHelpText(
+    'after',
+    `
+Examples:
+  warelay send --to +15551234567 --message "Hi"                # wait 20s for delivery (default)
+  warelay send --to +15551234567 --message "Hi" --wait 0       # fire-and-forget
+  warelay send --to +15551234567 --message "Hi" --wait 60 --poll 3`
+  )
+  .action(async (opts) => {
+    const waitSeconds = Number.parseInt(opts.wait, 10);
+    const pollSeconds = Number.parseInt(opts.poll, 10);
+
+    if (Number.isNaN(waitSeconds) || waitSeconds < 0) {
+      console.error('Wait must be >= 0 seconds');
+      process.exit(1);
+    }
+    if (Number.isNaN(pollSeconds) || pollSeconds <= 0) {
+      console.error('Poll must be > 0 seconds');
+      process.exit(1);
+    }
+
+    const result = await sendMessage(opts.to, opts.message);
+    if (!result) return;
+    if (waitSeconds === 0) return;
+    await waitForFinalStatus(result.client, result.sid, waitSeconds, pollSeconds);
+  });
+
+program
+  .command('monitor')
+  .description('Poll Twilio for inbound WhatsApp messages')
+  .option('-i, --interval <seconds>', 'Polling interval in seconds', '5')
+  .option('-l, --lookback <minutes>', 'Initial lookback window in minutes', '5')
+  .addHelpText(
+    'after',
+    `
+Examples:
+  warelay monitor                         # poll every 5s, look back 5 minutes
+  warelay monitor --interval 2 --lookback 30`
+  )
+  .action(async (opts) => {
+    const intervalSeconds = Number.parseInt(opts.interval, 10);
+    const lookbackMinutes = Number.parseInt(opts.lookback, 10);
+
+    if (Number.isNaN(intervalSeconds) || intervalSeconds <= 0) {
+      console.error('Interval must be a positive integer');
+      process.exit(1);
+    }
+    if (Number.isNaN(lookbackMinutes) || lookbackMinutes < 0) {
+      console.error('Lookback must be >= 0 minutes');
+      process.exit(1);
+    }
+
+    await monitor(intervalSeconds, lookbackMinutes);
+  });
+
+program
+  .command('webhook')
+  .description('Run a local webhook server for inbound WhatsApp (works with Tailscale/port forward)')
+  .option('-p, --port <port>', 'Port to listen on', '42873')
+  .option('-r, --reply <text>', 'Optional auto-reply text')
+  .option('--path <path>', 'Webhook path', '/webhook/whatsapp')
+  .addHelpText(
+    'after',
+    `
+Examples:
+  warelay webhook                       # listen on 42873
+  warelay webhook --port 45000          # pick a high, less-colliding port
+  warelay webhook --reply "Got it!"     # static auto-reply; otherwise use config file
+
+With Tailscale:
+  tailscale serve tcp 42873 127.0.0.1:42873
+  (then set Twilio webhook URL to your tailnet IP:42873/webhook/whatsapp)`
+  )
+  .action(async (opts) => {
+    const port = Number.parseInt(opts.port, 10);
+    if (Number.isNaN(port) || port <= 0 || port >= 65536) {
+      console.error('Port must be between 1 and 65535');
+      process.exit(1);
+    }
+    await startWebhook(port, opts.path, opts.reply);
+  });
+
+program
+  .command('setup')
+  .description('Auto-setup webhook + Tailscale Funnel + Twilio callback with sensible defaults')
+  .option('-p, --port <port>', 'Port to listen on', '42873')
+  .option('--path <path>', 'Webhook path', '/webhook/whatsapp')
+  .action(async (opts) => {
+    const port = Number.parseInt(opts.port, 10);
+    if (Number.isNaN(port) || port <= 0 || port >= 65536) {
+      console.error('Port must be between 1 and 65535');
+      process.exit(1);
+    }
+
+    // Validate env and binaries
+    const env = readEnv();
+    await ensureBinary('tailscale');
+
+    // Start webhook locally
+    await startWebhook(port, opts.path, undefined);
+
+    // Enable Funnel and derive public URL
+    await ensureFunnel(port);
+    const host = await getTailnetHostname();
+    const publicUrl = `https://${host}${opts.path}`;
+    console.log(`🌐 Public webhook URL (via Funnel): ${publicUrl}`);
+
+    // Configure Twilio sender webhook
+    const client = createClient(env);
+    const senderSid = await findWhatsappSenderSid(client, env.whatsappFrom);
+    await updateWebhook(client, senderSid, publicUrl, 'POST');
+
+    console.log('\nSetup complete. Leave this process running to keep the webhook online. Ctrl+C to stop.');
+  });
+
+program.parseAsync(process.argv);
diff --git a/tsconfig.json b/tsconfig.json
new file mode 100644
index 000000000..276dba974
--- /dev/null
+++ b/tsconfig.json
@@ -0,0 +1,18 @@
+{
+  "compilerOptions": {
+    "target": "ES2022",
+    "module": "NodeNext",
+    "moduleResolution": "NodeNext",
+    "outDir": "dist",
+    "rootDir": "src",
+    "strict": true,
+    "esModuleInterop": true,
+    "forceConsistentCasingInFileNames": true,
+    "skipLibCheck": true,
+    "resolveJsonModule": true,
+    "noEmitOnError": true,
+    "allowSyntheticDefaultImports": true
+  },
+  "include": ["src/**/*"],
+  "exclude": ["node_modules", "dist"]
+}