Selfhosted
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I did manage to get it to work, but I recall it took me a while. I have several devices connected to it now though. I'm keenly looking forward to the autogroup:self ACL support so I can set up sensible ACLs and share my net with some mates - I only have my own devices on it right now.
Anything I can share that might help your understanding?
Every system I can run headscale on I need to do it via an nginx reverse proxy
Yes you need a way to expose it over https. A reverse proxy is easiest. I use Caddy.