diff --git a/README.md b/README.md
index 9fe45cf..f768e11 100644
--- a/README.md
+++ b/README.md
@@ -93,3 +93,10 @@ pm2 reload tssbot-web --update-env
 Only processes listed in `PM2_RESTART_TARGETS` are reloaded. The default is
 `tssbot-web`, so unrelated PM2 processes are left alone. The webhook exits after
 24 hours so PM2 restarts it cleanly.
+
+The webhook listener reads `.env` on startup. To send a Discord notification
+whenever the listener starts or restarts, set:
+
+```sh
+DISCORD_WEBHOOK_URL=https://discord.com/api/webhooks/...
+```
diff --git a/ecosystem.config.cjs b/ecosystem.config.cjs
index 4872326..e43f6f0 100644
--- a/ecosystem.config.cjs
+++ b/ecosystem.config.cjs
@@ -24,6 +24,7 @@ module.exports = {
         WEBHOOK_PORT: process.env.WEBHOOK_PORT || 3011,
         GITHUB_WEBHOOK_SECRET: process.env.GITHUB_WEBHOOK_SECRET || '',
         PM2_RESTART_TARGETS: process.env.PM2_RESTART_TARGETS || 'tssbot-web',
+        DISCORD_WEBHOOK_URL: process.env.DISCORD_WEBHOOK_URL || '',
       },
     },
   ],
diff --git a/example.env b/example.env
index bcf00b4..e9a392f 100644
--- a/example.env
+++ b/example.env
@@ -10,3 +10,4 @@ API_RATE_LIMIT_MAX=120
 WEBHOOK_PORT=3011
 GITHUB_WEBHOOK_SECRET=change-me
 PM2_RESTART_TARGETS=tssbot-web
+DISCORD_WEBHOOK_URL=https://discord.com/api/webhooks/...
diff --git a/webhook.cjs b/webhook.cjs
index 6d7430d..09d13e8 100644
--- a/webhook.cjs
+++ b/webhook.cjs
@@ -1,9 +1,44 @@
 const crypto = require('node:crypto')
+const fs = require('node:fs')
 const http = require('node:http')
+const https = require('node:https')
+const os = require('node:os')
+const path = require('node:path')
 const { spawn } = require('node:child_process')
 
+function loadEnvFile() {
+  const envPath = path.join(__dirname, '.env')
+  if (!fs.existsSync(envPath)) return
+
+  const lines = fs.readFileSync(envPath, 'utf8').split(/\r?\n/)
+  for (const line of lines) {
+    const trimmed = line.trim()
+    if (!trimmed || trimmed.startsWith('#')) continue
+
+    const separatorIndex = trimmed.indexOf('=')
+    if (separatorIndex === -1) continue
+
+    const key = trimmed.slice(0, separatorIndex).trim()
+    let value = trimmed.slice(separatorIndex + 1).trim()
+
+    if (
+      (value.startsWith('"') && value.endsWith('"')) ||
+      (value.startsWith("'") && value.endsWith("'"))
+    ) {
+      value = value.slice(1, -1)
+    }
+
+    if (key && (!process.env[key] || process.env[key] === '')) {
+      process.env[key] = value
+    }
+  }
+}
+
+loadEnvFile()
+
 const PORT = Number(process.env.WEBHOOK_PORT || 3011)
 const SECRET = process.env.GITHUB_WEBHOOK_SECRET || ''
+const DISCORD_WEBHOOK_URL = process.env.DISCORD_WEBHOOK_URL || ''
 const RESTART_TARGETS = (process.env.PM2_RESTART_TARGETS || 'tssbot-web')
   .split(',')
   .map((target) => target.trim())
@@ -47,6 +82,69 @@ function run(command, args) {
   })
 }
 
+function postDiscordWebhook(payload) {
+  if (!DISCORD_WEBHOOK_URL) return Promise.resolve()
+
+  return new Promise((resolve) => {
+    let url
+    try {
+      url = new URL(DISCORD_WEBHOOK_URL)
+    } catch (error) {
+      console.error('Discord restart webhook URL is invalid:', error.message)
+      resolve()
+      return
+    }
+
+    const body = Buffer.from(JSON.stringify(payload))
+    const client = url.protocol === 'http:' ? http : https
+    const req = client.request(
+      url,
+      {
+        method: 'POST',
+        headers: {
+          'content-type': 'application/json',
+          'content-length': body.length,
+          'user-agent': 'tssbot-webhook',
+        },
+        timeout: 5000,
+      },
+      (res) => {
+        res.resume()
+        res.on('end', resolve)
+      },
+    )
+
+    req.on('timeout', () => {
+      req.destroy(new Error('Discord restart webhook timed out'))
+    })
+    req.on('error', (error) => {
+      console.error('Discord restart webhook failed:', error.message)
+      resolve()
+    })
+    req.end(body)
+  })
+}
+
+function notifyDiscordRestart() {
+  const startedAt = new Date()
+
+  postDiscordWebhook({
+    username: 'tssbot webhook',
+    embeds: [
+      {
+        title: 'Webhook listener restarted',
+        color: 0x00f2ff,
+        fields: [
+          { name: 'Host', value: os.hostname(), inline: true },
+          { name: 'Port', value: String(PORT), inline: true },
+          { name: 'Restart targets', value: RESTART_TARGETS.join(', ') || 'none', inline: false },
+        ],
+        timestamp: startedAt.toISOString(),
+      },
+    ],
+  })
+}
+
 async function deploy() {
   await run('git', ['pull', '--ff-only'])
   await run('npm', ['install'])
@@ -103,6 +201,7 @@ http
   .listen(PORT, '0.0.0.0', () => {
     console.log(`tssbot webhook listening on http://localhost:${PORT}/github`)
     console.log(`restart targets: ${RESTART_TARGETS.join(', ')}`)
+    notifyDiscordRestart()
   })
 
 setTimeout(() => {