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Then I guess you only define an A record in the DuckDNS panel. That's fine.
A while back I ran a somewhat similar Wireguard tunnel and can't connect. Turns out some MTU settings were lower than the docker's MTU and that breaks big packets like SSL handshakes. Restarting makes it work fine until things start congesting again.
Suffice to say this would be something I'll look at if the SSL errors reoccurs
So the MTU of Tailscale is actually 1280, but is the connection even going through the VPN or rather through my VPS, when Uptime-Kuma is trying to connect to my local domain?
It shouldn't go through the VPN although idk how to verify that. Do you still have the timeout errors in your monitors? What do those errors say?
Thanks, since I access my home network and server through the public IPv4 of a VPS via Tailscale this could actually be the issue. I'll look into it, when I find the time.