For those still having issues with this I was able to solve by doing the following: Leave Plex in host mode. Set Transmission-OpenVPN container to bridge mode. Host = your server IP. Port = 9091. If you make these changes and can no longer access the Transmission web gui - modify your docker container and verify that the LOCAL_NETWORK environmental variable is set to the correct IP address range (i.e. 192.168.1.0/26) for your network. Transmissions web gui should now be available.