Naming tv show with multiple seasons in single file

[OttoKerner]

It is not possible. You cannot have files which cross the season boundary in Plex.

I recommend you to split your files.
Only then all the features related to tv shows work correctly.

[HowTo]: splitting multi-episode files with MKVtoolnix GUI

The purpose of this HowTo is to split videofiles which contain more than one episode of a tv show into single-episode files. So they show up individually within plex, can be played individually and don’t produce any of the weird things that multi-episode files are plagued with. The tool used is MKVtoolnixGUI it is freely available for all major PC operating systems. Therefore the container format of the output files will be MKV. The input format can be a multitude of containers like AVI, MP4…