Plex has gone ‘round the bend’ with this TV Show naming thing and it’s causing no shortage of pain and suffering all around.
Try this - experience (and testing) dictates it will work:
TV Shows
----Taken (2002)
--------Season 1
------------Taken (2002) s01e01.avi
------------Taken (2002) s01e02.avi
------------etc.
----Taken (2017)
--------Season 1
------------Taken (2017) s01e01.mkv
------------Taken (2017) s01e02.mkv
------------etc.
A Plex Dance® is required:
The Plex Dance®:
- remove shows from library - Yep, the whole things - both of them. It’s a ‘do-over’.
- 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 - at this point compliance is an adventure.
- replace corrected show into library
- update library
All Steps. In Order. No Shortcuts.
The above naming will work. I had the ‘old’ Taken aboard, matched before Plex lost it’s mind, but just now re-matched my old version and the new version with a ‘test show’ just for you: