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Well first I’d try turning off pi hole on the server avenue see if it fixes the issue, even though it’s unlikely as pihole should be handling dns requests for your whole network anyway.
Usually with this setup you only need to place your torrent/Usenet download client behind the VPN. Use a container like gluetun and make your download client container a service of gluetun so it only connects though gluetun. The rest of your stack can just access the internet normally.
There should be more info in the jellyseer log file, have a look in your docker directory or have a play with the "docker logs" command and try to recreate the issue. If you kill your jellyseer container then start it
You were right, it wasn't the pihole. I managed to get the system running by whitelisting my LAN in my VPN, which I've never had to do before. I'll certainly look into creating services with gluetun, though! Thanks!
Just to close off this thread, you were 100% right about using Gluetun as well.
After I got everything working nicely (pre-Gluetun), I got a strange email from my ISP about allegedly copyrighted material being made available by someone or other on my home IP. No idea who that could be.
Turns out, friends, that VPNs sometimes silently drop connection. And the killswitch may block the traffic of the user that initiated the VPN connection, but it not does not block Transmission traffic inside a docker container. That was a bummer to find out the hard way. Anyway, running the VPN in a Gluetun container and making it a service of the Transmission container solves that problem rather nicely and is surprisingly easy to implement. Thanks to the developer for that, and thanks to you for pointing me down the right path!