We hired one of the Headscale developers and let him work on it (as part of his job, not just moonlighting) and we help out when there are issues and give them a heads-up when protocol changes/etc are coming.

This is such an outstanding response to the existence of Headscale that I struggle to understand it. Why not just open source Tailscale's control server? Don't get me wrong though, what you guys are doing now is great.

Edit: some explanation here: https://tailscale.com/blog/opensource/

My guess would have to be that their version is probably deeply integrated with the rest of the product and infra that it doesn’t make sense.

Plus there’s the added benefit to their paying customers to know that we have an out if needed. It reduces friction in starting to use the product.

There’s another added benefit that they get two different implementations of the same protocol. When you have multiple implementations, you effectively have a double check on the protocol design. This should make the project as a whole significantly better engineered.

It’s quite clever from Tailscale.

Or their own server is too big for small use so not welcomed by selfhoster, like Bitwarten/Vaultwarden case.

Yeah, that's probably very true. Our main coordination server should probably get easier to run (for our on-prem customers and our various country-specific instances we run) but Headscale is far ahead of Tailscale's on just being easy to run.

That's great news! Makes me confident to actually try out headscale+ tailscale! Thank you.