I'm sorry I'm still new to Tailscale so I'm not sure what I can provide that would be of assistance. I finally got Tailscale + Caddy to work on my home network so that I can type `jellyfin[.]mydomain[.]com`. This weekend is my first weekend away from home and I was trying to test the remote connection and it worked on my iPhone & iPad, but it doesn't work on my Mac.
The Cloudflare DNS record is: `*.mydomain.com A <Caddy IP Address>`. It is working since I can get the domain working on my iPhone and iPad.
The issue is just the Mac. I've tried stopping and starting the Tailscale connection on my Mac to no avail. I also just tried uninstalling Tailscale on my Mac and reinstalling. Still no luck. I also tried turning off my VPN on my Mac – nothing. When I'm connected to Tailscale (yes the correct tailnet) on my Mac, I can `ping <Caddy IP Address>` and I can also `ping caddy.*.ts.net` (Caddy's FQDN on my tailnet).
I can see on the Tailscale admin/machine dashboard that my Mac is connected, just like Caddy and my iPad. What's weird is I can no longer `dig mydomain[.]com` or `dig jellyfin[.]mydomain[.]com`.
Any assistance would be very much appreciated. If there is any logs or additional information I can provide please let me now. I don't think this is a Cloudflare problem since my iPhone and iPad work as expected. It's either an issue with my Mac or Tailscale.
Source: r/Tailscale · by /u/0xmaboro