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Swapping VPN for Tailscale: A Five-Day Internal Infra Upgrade

originally posted at LinkedIn at June 25, 2025

We recently started migrating away from our traditional VPN setup—and toward something simpler, faster, and cheaper: Tailscale.

This wasn’t a full rip-and-replace. In just five days, we moved a core set of internal Kubernetes services behind Tailscale, enough to start retiring our legacy VPN setup piece by piece.

The results?
✅ Smoother developer workflows
✅ Better access control
✅ Significant cost savings
✅ Self-serve onboarding
✅ Fewer support headaches

Enjoy Super Speeding in Private Network Tunnel

Automated TLS and DNS in Kubernetes with ExternalDNS, Ingress, and Let's Encrypt

Managing DNS and TLS certificates for Kubernetes applications can be tedious and error-prone. Thankfully, tools like ExternalDNS, Ingress, and Cert-Manager automate the entire process — from setting DNS records to provisioning Let's Encrypt certificates.

In this guide, we'll walk through how to:

  • Use ExternalDNS to automatically create DNS records.
  • Annotate Ingress resources to request a Let's Encrypt TLS cert.
  • Get HTTPS with minimal manual intervention.
  • Understand how these components interact.

Auto TLS and DNS with ExternalDNS, Ingress, and Let's Encrypt