Windsurf
email
Nodemailer TLS Handshake Failed in Windsurf App
Your Windsurf-generated app fails to send emails through Nodemailer with TLS handshake errors. Email functionality that worked in development breaks when deployed, or stops working suddenly after the email provider updates their security settings.
TLS (Transport Layer Security) handshake failures mean your app cannot establish a secure connection to the SMTP server. This blocks all email sending — password resets, notifications, verification emails, and any other transactional emails your app depends on.
The error may be intermittent, working sometimes and failing others, or it may fail consistently after a deployment or SMTP provider change. Common scenarios include moving from development to production, switching email providers, or the provider deprecating old TLS versions.
Error Messages You Might See
Error: self-signed certificate
Error: unable to verify the first certificate
Error: ESOCKET - TLS handshake failed
Error: Connection timeout on port 465
Error: SSL routines:ssl3_get_record:wrong version number
Common Causes
- Wrong port and security combination — Cascade configured port 465 with STARTTLS (should use TLS) or port 587 with direct TLS (should use STARTTLS)
- Self-signed or expired certificate — The SMTP server's SSL certificate is self-signed, expired, or not trusted by Node.js
- TLS version mismatch — The SMTP server requires TLS 1.2+ but the Node.js configuration allows old versions, or vice versa
- rejectUnauthorized set incorrectly — Cascade set rejectUnauthorized: false during development to bypass cert errors, but this is insecure for production
- Firewall blocking SMTP ports — The hosting platform (Vercel, Railway, etc.) blocks outbound SMTP connections on ports 25, 465, or 587
How to Fix It
- Match port to security protocol — Use port 587 with secure: false (STARTTLS upgrades automatically), or port 465 with secure: true (implicit TLS). Never use port 25 for authenticated email
- Verify SMTP credentials — Double-check host, port, username, and password. Many providers require app-specific passwords when 2FA is enabled
- Set proper TLS options — Add tls: { minVersion: 'TLSv1.2', rejectUnauthorized: true } to your Nodemailer transport configuration
- Test SMTP connection independently — Use the nodemailer verify() method to test the connection before sending: transporter.verify().then(console.log).catch(console.error)
- Use an email API instead — If your host blocks SMTP ports, switch from Nodemailer SMTP to an HTTP-based email API (SendGrid, Resend, Postmark) that uses port 443
- Check your hosting platform — Vercel, Netlify, and some serverless platforms block SMTP. Check their docs for email sending limitations
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Get HelpFrequently Asked Questions
Should I use port 465 or 587 for sending email?
Use port 587 with STARTTLS for most modern SMTP providers. Port 587 starts unencrypted and upgrades to TLS. Port 465 uses implicit TLS and is the legacy standard. Set secure: false for port 587 (Nodemailer handles STARTTLS automatically) and secure: true for port 465.
Is it safe to set rejectUnauthorized: false?
No. Setting rejectUnauthorized: false disables certificate validation, making your connection vulnerable to man-in-the-middle attacks. Only use it for local development. In production, fix the certificate issue instead.