Stuck indefinitely on “… Waiting to be converted”

I’m seeing a problem where videos selected to sync with my mobile (android) devices get stuck indefinitely on “… Waiting to be converted”, even after letting it go overnight without any other sync’s. other tv shows and movies sync fine and start immediately.

Does anyone have any troubleshooting guidance, log analysis, etc…?

I’m running Version 1.13.8.5395 on a fedora 28 vm.Plex Media Server.log…zip (230.1 KB)

update: when I try to manually optimize, i get the errror “Converted files cannot be written to the server’s disk” despite having about 230gb free.