@ricm916 I actually think there might be something going on beyond just an issue with your setup. I've had DNS resolution issues pop-up several times this week in a similar chain with Proxmox, Docker and Tailscale. Both times I've been able to "fix" it, though I'm not so sure it didn't simply start working again.
You didn't mention it as part of your setup, but in my case, I also have MagicDNS with dual Pi-hole servers in the mix. I haven't been able to put my finger on exactly where resolution is going off the rails, but for now I've added my LAN's domain (localdomain) to my tailnet (tailxxxxx.ts.net) in containers where I'm specifying dns_search:
You may want to try this container again today to see if the issue is resolved, as my best WAG at this point is that it's Tailscale infrastructure related, with perhaps a dash of Docker thrown-in. Tailscale has had several updates in the last week, including 1.66.4 that claims to have fixed some form of inadvertently broken DNS resolution in 1.66.3.




