https://support.plex.tv/articles/categories/media-preparation/
https://support.plex.tv/articles/200220687-naming-series-season-based-tv-shows/
In the case of M4V/MP4 files:
Plex will read bogus embedded Title Fields and prefer them over a perfect file name/structure (borking your match in the process), but you can combat that situation by moving Local Media Assets to the bottom of every agent list you can find. All tabs in TV Shows and Movies here:
https://support.plex.tv/hc/en-us/articles/200241558-Agents
Just drag LMA to the bottom of the list and drop it. If you do have embedded metadata this will cure the issue, if you don’t it won’t matter. LMA will do what it has to from the bottom.
Renaming/restructuring is best performed OUTSIDE the library and you may need to write a new bundle for the show or movie so The Plex Dance® was invented:
The Plex Dance®:
- remove show/movie from library
- rescan library files
- empty trash
- clean bundles
https://support.plex.tv/hc/en-us/articles/200392106-Library-Actions <— scan library files, empty trash, clean bundles - bring names and structures into compliance/Move LMA/etc
- replace corrected show/movie into library
- rescan library files
All Steps. In Order. No Shortcuts.