this post was submitted on 30 Aug 2023
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How do you use Tailscale? (sh.itjust.works)
submitted 1 year ago by [email protected] to c/selfhosted
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I've read a lot of recommendations for tailscale and am on my way to try it out myself. Do you use Tailscale in the "normal" way or do you host your own Headscale server (as I'm planning to do)? Any pros and cons?

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[–] PriorProject 14 points 1 year ago* (last edited 1 year ago) (2 children)

I use Headscale, but Tailscale is a great service and what I generally recommend to strangers who want to approximate my setup. The tradeoffs are pretty straightforward:

  • Tailscale is going to have better uptime than any single-machine Headscale setup, though not better uptime than the single-machine services I use it to access... so not a big deal to me either way.
  • Tailscale doesn't require you to wrestle with certs or the networking setup required to do NAT traversal. And they do it well, you don't have to wonder whether you've screwed something up that's degrading NAT traversal only in certain conditions. It just works. That said, I've been through the wringer already on these topics so Headscale is not painful for me.
  • Headscale is self-hosted, for better and worse.
  • In the default config (and in any reasonable user-friendly, non professional config), Tailscale can inject a node into your network. They don't and won't. They can't sniff your traffic without adding a node to your tailnet. But they do have the technical capability to join a node to your tailnet without your consent... their policy to not do that protects you... but their technology doesn't. This isn't some surveillance power grab though, it's a risk that's essential to the service they provide... which is determining what nodes can join your tailnet. IMO, the tailscale security architecture is strong. I'd have no qualms about trusting them with my network.
  • Beyond 3 ~~devices~~ users, Tailscale costs money... about $6 US in that geography. It's a pretty reasonable cost for the service, and proportional in the grand scheme of what most self-hosters spend on their setups annually. IMO, it's good value and I wouldn't feel bad paying it.

Tailscale is great, and there's no compelling reason that should prevent most self-hosters that want it from using it. I use Headscale because I can and I'm comfortable doing so... But they're both awesome options.

[–] [email protected] 11 points 1 year ago (1 children)

Beyond 3 devices, Tailscale costs money

I think you mean beyond 3 users. You are allowed up to 100 devices in the free tier.

[–] PriorProject 4 points 1 year ago

Yeah, misread the pricing page. Fixed the post, thanks for the correction.

[–] [email protected] 2 points 1 year ago (1 children)

Tailscale doesn’t require you to wrestle with certs or the networking setup required to do NAT traversal. And they do it well, you don’t have to wonder whether you’ve screwed something up that’s degrading NAT traversal only in certain conditions. It just works. That said, I’ve been through the wringer already on these topics so Headscale is not painful for me.

Does Headscale require additional work to deal with NAT traversal on clients? Or is it just for the controller node itself?

[–] PriorProject 1 points 1 year ago

You connect to Headscale using the tailscale clients, and configuration is exactly the same irrespective of which control server you use... with the exception of having to configure the custom server url with Headscale (which requires navigating some hoops and poor docs for mobile/windows clients).

But to my knowledge there are no client-side configs related to NAT traversal (which is kind of the goal... to work seamlessly everywhere). The configs themselves on the headscale server aren't so bad either, but the networking concepts involved are extremely advanced, so debugging if anything goes sideways or validating that your server-side NAT traversal setup is working as expected can be a deep dive. With Tailscale, you know any problems are client-side and can focus your attention accordingly... which simplifies initial debugging quite a lot.