Your file naming sucks. Badly.
Those don’t suck.
Another reason could be a contributing factor is your file type. Mine are MKVs. If your are MP4/M4V… do this:
Then Refresh Metadata for the show you’re working on.
Between lousy file name and structure fixing - and removing the possibility for embedded metadata in MP4/M4V files from interfering - this issue should resolve itself… I hope.
https://support.plex.tv/articles/naming-and-organizing-your-tv-show-files/
https://support.plex.tv/articles/naming-and-organizing-your-movie-media-files/
