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
