06-29-2026, 08:52 PM
Been running Tailscale for about 18 months across my home lab, a VPS, and a few travel devices. Before that I ran WireGuard manually for two years.
Why I moved to Tailscale:
What I gave up:
Verdict: Tailscale for personal use and small teams, self-hosted WireGuard when the org has a dedicated network person and a reason to avoid third-party control planes.
What are you running?
Why I moved to Tailscale:
- NAT traversal just works. WireGuard requires at least one public endpoint. Tailscale handles the CGNAT case without me thinking about it.
- Device management is actually pleasant. Adding a new machine is under 2 minutes.
- MagicDNS is underrated. Referring to machines by name instead of IP removes a whole class of confusion.
What I gave up:
- Control plane is in Tailscale hands. If you have strict self-sovereignty requirements this is a non-starter.
- Headscale exists but the setup overhead partially defeats the convenience argument.
- The free tier is 3 users and used to be more generous.
Verdict: Tailscale for personal use and small teams, self-hosted WireGuard when the org has a dedicated network person and a reason to avoid third-party control planes.
What are you running?