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
Real developers can help you.
Milan Surelia
Milan Surelia is a Mobile App Developer with 5+ years of experience crafting scalable, cross-platform apps at 7Span and Meticha. At 7Span, he engineers feature-rich Flutter apps with smooth performance and modern UI. As the Co-Founder of Meticha, he builds open-source tools and developer-focused products that solve real-world problems.
Expertise:
💡 Developing cross-platform apps using Flutter, Dart, and Jetpack Compose for Android, iOS, and Web.
🖋️ Sharing insights through technical writing, blogging, and open-source contributions.
🤝 Collaborating closely with designers, PMs, and developers to build seamless mobile experiences.
Notable Achievements:
🎯 Revamped the Vepaar app into Vepaar Store & CRM with a 2x performance boost and smoother UX.
🚀 Launched Compose101 — a Jetpack Compose starter kit to speed up Android development.
🌟 Open source contributions on Github & StackOverflow for Flutter & Dart
🎖️ Worked on improving app performance and user experience with smart solutions.
Milan is always happy to connect, work on new ideas, and explore the latest in technology.
Basel Issmail
’m a Senior Full-Stack Developer and Tech Lead with experience designing and building scalable web platforms. I work across the full development lifecycle, from translating business requirements into technical architecture to delivering reliable production systems.
My work focuses on modern web technologies, including TypeScript, Angular, Node.js, and cloud-based architectures. I enjoy solving complex technical problems and helping teams turn product ideas and prototypes into working platforms that can grow and scale.
In addition to development, I often collaborate closely with product managers, business analysts, designers, and QA teams to ensure that solutions align with both technical and business goals.
I enjoy working with startups and product teams where I can contribute both as a hands-on engineer and as a technical partner in designing and delivering impactful software.
Yovel Cohen
I got a lot of experience in building Long-horizon AI Agents in production, Backend apps that scale to millions of users and frontend knowledge as well.
Vlad Temian
15+ years shipping production infrastructure for startups. Former CTO at qed.builders (acquired by The Sandbox).
Cursor ambassador and agentic tooling builder.
I've scaled systems, automated deployments, and built observability tools for AI coding workflows. I specialize in taking vibe-coded apps from broken prototype to production-ready: fixing Supabase auth/RLS, Stripe integrations, deployment pipelines, and cleaning up AI-generated spaghetti.
I build tools in this space (agentprobe, claudebin, micode) and understand both sides: how AI generates code and why it breaks.
https://blog.vtemian.com/
Luca Liberati
I work on monoliths and microservices, backends and frontends, manage K8s clusters and love to design apps architecture
Taufan
I’m a product-focused engineer and tech leader who builds scalable systems and turns ideas into production-ready platforms.
Over the past years, I’ve worked across startups and fast-moving teams, leading backend architecture, improving system reliability, and shipping products used by thousands of users. My strength is not just writing code — but connecting product vision, technical execution, and business impact.
Jacek Rozanski
Senior PHP/Symfony developer and DevOps engineer with 20+ years of professional experience, running opcode.pl (web development agency, est. 2004).
Day job: I'm the sole backend developer at merketing company where I own and maintain 11 PHP/Symfony microservices on AWS (ECS Fargate, RDS, S3, CloudFront), handle the full CI/CD pipeline (Bitbucket Pipelines, Docker), and manage monitoring with Sentry and CloudWatch. These services handle high request volumes in production every month.
What I bring to AI-built apps:
- I audit and fix security issues (OWASP methodology), performance bottlenecks, and architectural problems in codebases generated by Cursor, Claude Code, Lovable, Bolt, and v0
- I refactor AI-generated prototypes into production-grade applications with proper error handling, testing, and clean architecture (SOLID, DDD, hexagonal architecture)
- I set up the infrastructure AI tools don't touch: AWS hosting, CI/CD pipelines, automated deployments, database optimization, monitoring, and alerting
- I integrate external services: payment providers, email systems, partner APIs, SSO/auth
Tech stack: PHP 8.x, Symfony, React, Next.js, PostgreSQL, MySQL, Docker, AWS (ECS, RDS, S3, SQS/SNS, CloudFront), Terraform, Supabase. I also use AI tools daily (Claude Code, Cursor) in my own workflow, so I understand both the strengths and the gaps in AI-generated code.
Based in Poland (CET timezone). Available for async work and calls during EU/US business hours.
BurnHavoc
Been around fixing other peoples code for 20 years.
Stanislav Prigodich
15+ years building iOS and web apps at startups and enterprise companies. I want to use that experience to help builders ship real products - when something breaks, I'm here to fix it.
Jared Hasson
Full time lead founding dev at a cyber security saas startup, with 10 yoe and a bachelor's in CS. Building & debugging software products is what I've spent my time on for forever
You don't need to be technical. Just describe what's wrong and a verified developer will handle the rest.
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.