I reinstalled 1.18.4.2171-ac2afe5f8 (free BSD) turned on debug logging and set up two new sync sessions with two different TV shows. one is to iOS and the other to Android. I also made a minor change to the network configuration using a different NIC.
Same result as OP. conversion takes place, the devices see the new episodes available in sync->manage, but download never starts.
Logs enclosed.
Thanks.
Plex Media Server Logs_2020-01-07_23-32-08.zip (2.4 MB)
FYI;
After posting this, I downgraded to 1.18.3.2156-349e9837e, and restarted the sync on both devices, they began downloading the episodes.
