this post was submitted on 18 Mar 2025
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Did anyone paranoid like me research security implications of running Tailscale/Headscale or similiar?

Right now I'm self-hosting headscale controller in my LAN and expose it to public Internet. I'm thinking about moving it to a VPS, but I'm a little paranoid about exposing the software that controls connectivity between my and family machines to a third party, be it official Tailscale controller or VPS provider where I run Headscale.

Currently I think that even in the worst case of someone compromising my Headscale instance it should still be fine as long as all of the machines are properly firewalled and all of the exposed apps and services are behind authentication. I run everything behind Authentik and only keys for SSH access. I will certainly add some network monitoring to all of that.

Any opions and suggestions on this matter are welcome.

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So the general tailscale actually uses peer to peer wiregaurd connections. Headscale is the middle point to negotiate these wiregaurd connections.

So none of the traffic moves through the VPS.

As for a VPS itself, it's noore unsafe than your local bare metal. It's still an application publicly exposed and needs basic precautions like fail2ban or crowdsec