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.

  • BCsvenEnglish
    3·
    22 hours ago

    I can’t offer technical network advice on vps headscale; Personally I’m not confident in my network skills. I would be more inclined to go through the pain of manually setting up wireguard instead of having a tailscale or headscale service-- and skipping the middleman so to speak.

    Edit: setting up a new system this month, Tumbleweed has moved to SE Linux Enforcing as default. It provided some ssh and samba challenges at first until I learned about setting SEL policies. So maybe hardening with SE Linux would also be smart. For example I could SSH remotely into my machine but due to policies being locked down I could not run user bash, or even see contents of the home folder.

    • McMonster@programming.devOPEnglish
      3·
      21 hours ago

      Thanks. Plain Wireguard is an option I’m considering, but it’s also considerably more hassle to configure and maintain, especially as I connect more family members to my network. Headscale also has an extra layer of security in the form of ACLs, which I plan to use on top of basic firewall configuration. I do connect my personal machines with Wireguard, but I use one family member as a Tailscale/Headscale test subject.

      As for SELinux, I’ve gave up on it already. It caused me so much headache over the years I disable it with a kernel parameter by default on all machines.

      • BCsvenEnglish
        3·
        21 hours ago

        Yeah it definitely is a pain for adding multiple machines.