Tailscale keeps a soft node cap on the free plan, so past that point the migration is not about price but topology control: headscale puts the coordination plane on hardware you can reason about, and the ACL rules stop being a hosted black box. The underestimated part is DERP: self-hosting the relay is what fixes latency on restricted paths, and it is also the piece that breaks first when the upstream service changes behavior.
Tailscale keeps a soft node cap on the free plan, so past that point the migration is not about price but topology control: headscale puts the coordination plane on hardware you can reason about, and the ACL rules stop being a hosted black box. The underestimated part is DERP: self-hosting the relay is what fixes latency on restricted paths, and it is also the piece that breaks first when the upstream service changes behavior.