Been testing Tailscale for a month to connect my Windows 10 desktop and an Ubuntu server. It's mostly fine, but hit some real headaches.
On Windows, the client sometimes just stops routing traffic after sleep. Have to disable/re-enable the adapter. The "always on" setting feels like a lie. On Linux, the CLI is okay, but if you mess with systemd-resolved, expect DNS to break completely. Had to manually set my DNS servers again. Also, the admin console is confusing about access controls. Almost opened my server up too wide by accident. Not paying for this until it's solid. Anyone else run into this or found fixes?
Totally feel you on the Windows sleep issue. I've seen the same thing with a few machines on our team. We found setting Tailscale as a "persistent" service in the Windows Services console (set to Automatic restart) reduced the frequency, but it still happens after a really deep sleep.
For the admin console, oh yeah. Their default ACLs are permissive. I nearly made the same mistake during our security review. I'd suggest drafting your access rules offline first, then pasting them in. It's easier to audit that way.
On the Linux DNS, we sidestepped it by just not using Tailscale's MagicDNS and sticking with static entries in our /etc/hosts file for the few nodes we needed. Not elegant, but stable.
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