Naming is absolutely the issue.
Tom has it right - you have it wrong.
Here are the instructions - if you want Plex to behave as expected - follow them:
https://support.plex.tv/articles/categories/your-media/naming-and-organizing-tv-shows/
Local Media Assets should always be enabled so it can use nifty things like Subtitles and images and all sorts of other Local Media Assets.
Local Media Assets should be ‘DEMOTED’ to the bottom of every agent list in Shows and Movies and here’s why:
When at the top, LMA tells Plex to inspect, find and use bogus embedded metadata in the Title Field of MP4/M4V files rendering them basically useless if, as most do, contain some off-the-wall Title some internet Bozo decided to infect your file with - or your friendly encoder software developer doesn’t give you an option to remove said crap from the files you make - and if you’re making MP4/M4V files - ur screwed.
Do this:
Plex will immediately STOP giving priority to Embedded Title Fields in MP4.M4V files (yes, even over a perfect file name), blowing the match and generally making your life miserable.
While you’re renaming these files in full view of Plex (watching your every move, writing/re-writing/confusing itself inside your item bundle) - so they’ll be compliant in both name and structure you may find Plex uncooperative in the area of Refreshing Metadata - as in it won’t update any metadata (even when you do it at the Show Level, where it’ll actually do something - sometimes).
Do this:
Need a new bundle?
The Plex Dance to create a new one.
Many do.
Let’s try to get all the right stuff in this new one.
The above is what - eventually - happens when you don’t follow the instructions.
This’ll help - it’ll basically do it for you: