Installing headscale on OpenBSD
Source: zakaria - Published on 2022-02-15 and updated on 2025-11-20 Note: This guide is severely out of date. The author recommends using ssl-proxy instead of relayd due to changes in the Tailscale protocol regarding web-sockets. In this post I’ll detail the steps I took to install and configure headscale, an open-source self-hostable implementation of the Tailscale control server, on OpenBSD. Code blocks prefixed with # imply that the command should be run as a privileged user/root. ...