this does pretty good on movies but horrible on tv shows…Branded 1965 with chuck conners
Harold, you really aren’t giving anyone enough info.
I can say that for my 40-50 different shows, Plex does wonderfully.
However, you have to make sure that movies and TV shows are not in the same library together.
And, though Plex tries to guess, you have to do a bit of file naming to give it a fighting chance.
https://support.plex.tv/hc/en-us/categories/200028098-Media-Preparation
I’ll echo this bit - 'cause it just can’t be echoed enough:
https://support.plex.tv/hc/en-us/categories/200028098-Media-Preparation
Not following this guide for TV Shows is a sure path to pain and suffering (TV Shows simply won’t work).
Branded: http://thetvdb.com/?tab=series&id=72699&lid=7
A TV Show Library/
…Branded/
…Season 01/
…Branded - S01E01.xxx
…etc…
…Season 02/
…Branded - S02E01.xxx
…etc…
FileBot (link in my signature) can handle that for you automatically or manually in seconds.
What FileBot can’t do is remove possible embedded metadata in the Title Field of MP4/M4V files. Plex will read this info and prefer it over a perfect file name/structure (you may not have any of those yet), 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 Show 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. This ONLY matters if you’re using MP4/M4V files - or ever want to.
Renaming/restructuring is best performed OUTSIDE the library and you’ll need to write a new bundle for the show so The Plex Dance® was invented:
The Plex Dance®:
- remove show/movie from library
- update library
- empty trash
- clean bundles
https://support.plex.tv/hc/en-us/articles/200392106-Library-Actions <— update library, empty trash, clean bundles - bring names and structures into compliance
- replace corrected show/movie into library
- update library
All Steps. In Order. No Shortcuts.
@juicewsa - fyi - typo in your example on season 2 folder.
@Harold4187 - what we said. 
Yep… repaired… thx.