Is the windows side up to date? Most likely culprit would be a db mismatch if one side or the other is on a different version. Similarly, do you by chance have either side running a beta release? If you have plex pass you potentially have access to these
Shameless moment to plug the idea that you could consider migrating to Jellyfin if you can’t solve the issue
It’d be really funny if it turned out the one person from Philly was him