Without knowing if the files are MP4/MKV/Other - or knowing what they are - or without knowing how they’re named and structured - Try this:
If that doesn’t work:
Server/Settings/General:
Enable Debug Logging
Disable Verbose Logging
Plex Dance a show or movie that’s misbehaving - see what happens - wait 5 minutes Get some logs:
Server/Settings/Troubleshooting
Drag zip file to message window and drop it.
Then we’ll know a lot more than we know right now.
ALL Steps
In Order
(or it won’t work)