From 1b28bd96d40d775a267972cdb6d2921a03565f03 Mon Sep 17 00:00:00 2001
From: jubnl <jgunther021@gmail.com>
Date: Wed, 1 Apr 2026 04:33:17 +0200
Subject: [PATCH] fix: encrypt SMTP password at rest using AES-256-GCM

The smtp_pass setting was stored as plaintext in app_settings, exposing
SMTP credentials to anyone with database read access. Apply the same
encrypt_api_key/decrypt_api_key pattern already used for OIDC client
secrets and API keys. A new migration transparently re-encrypts any
existing plaintext value on startup; decrypt_api_key handles legacy
plaintext gracefully so in-flight reads remain safe during upgrade.
---
 server/src/db/migrations.ts          | 7 +++++++
 server/src/routes/auth.ts            | 3 ++-
 server/src/services/notifications.ts | 3 ++-
 3 files changed, 11 insertions(+), 2 deletions(-)

diff --git a/server/src/db/migrations.ts b/server/src/db/migrations.ts
index 37e5c4f..435eda0 100644
--- a/server/src/db/migrations.ts
+++ b/server/src/db/migrations.ts
@@ -456,6 +456,13 @@ function runMigrations(db: Database.Database): void {
         db.prepare("UPDATE app_settings SET value = ? WHERE key = 'oidc_client_secret'").run(encrypt_api_key(row.value));
       }
     },
+    // Encrypt any plaintext smtp_pass left in app_settings
+    () => {
+      const row = db.prepare("SELECT value FROM app_settings WHERE key = 'smtp_pass'").get() as { value: string } | undefined;
+      if (row?.value && !row.value.startsWith('enc:v1:')) {
+        db.prepare("UPDATE app_settings SET value = ? WHERE key = 'smtp_pass'").run(encrypt_api_key(row.value));
+      }
+    },
   ];
 
   if (currentVersion < migrations.length) {
diff --git a/server/src/routes/auth.ts b/server/src/routes/auth.ts
index 679d20d..d1b211c 100644
--- a/server/src/routes/auth.ts
+++ b/server/src/routes/auth.ts
@@ -18,7 +18,7 @@ import { randomBytes, createHash } from 'crypto';
 import { revokeUserSessions } from '../mcp';
 import { AuthRequest, OptionalAuthRequest, User } from '../types';
 import { writeAudit, getClientIp } from '../services/auditLog';
-import { decrypt_api_key, maybe_encrypt_api_key } from '../services/apiKeyCrypto';
+import { decrypt_api_key, maybe_encrypt_api_key, encrypt_api_key } from '../services/apiKeyCrypto';
 import { startTripReminders } from '../scheduler';
 
 authenticator.options = { window: 1 };
@@ -665,6 +665,7 @@ router.put('/app-settings', authenticate, (req: Request, res: Response) => {
       }
       // Don't save masked password
       if (key === 'smtp_pass' && val === '••••••••') continue;
+      if (key === 'smtp_pass') val = encrypt_api_key(val);
       db.prepare("INSERT OR REPLACE INTO app_settings (key, value) VALUES (?, ?)").run(key, val);
     }
   }
diff --git a/server/src/services/notifications.ts b/server/src/services/notifications.ts
index 53e4e5c..06f5f76 100644
--- a/server/src/services/notifications.ts
+++ b/server/src/services/notifications.ts
@@ -1,6 +1,7 @@
 import nodemailer from 'nodemailer';
 import fetch from 'node-fetch';
 import { db } from '../db/database';
+import { decrypt_api_key } from './apiKeyCrypto';
 import { logInfo, logDebug, logError } from './auditLog';
 
 // ── Types ──────────────────────────────────────────────────────────────────
@@ -32,7 +33,7 @@ function getSmtpConfig(): SmtpConfig | null {
   const host = process.env.SMTP_HOST || getAppSetting('smtp_host');
   const port = process.env.SMTP_PORT || getAppSetting('smtp_port');
   const user = process.env.SMTP_USER || getAppSetting('smtp_user');
-  const pass = process.env.SMTP_PASS || getAppSetting('smtp_pass');
+  const pass = process.env.SMTP_PASS || decrypt_api_key(getAppSetting('smtp_pass')) || '';
   const from = process.env.SMTP_FROM || getAppSetting('smtp_from');
   if (!host || !port || !from) return null;
   return { host, port: parseInt(port, 10), user: user || '', pass: pass || '', from, secure: parseInt(port, 10) === 465 };