Four Years with Tailscale: Advanced Tips and Tricks

This post details four years of experience using Tailscale, a WireGuard orchestration service, for connecting disparate devices, servers, and apps. The author covers basic connectivity, SSH support, MagicDNS, service exposure (funnel and serve commands), custom authentication with KeyCloak, and ACLs and tags. The post also recounts troubleshooting experiences, such as incorrectly using tags and losing SSH access. Best practices are outlined, and the free personal plan is highly recommended.