Please provide a directory listing, screenshot, etc showing how you have the directories and files named and structured.
Plex is very picky with TV shows. If you have not done so, review the TV show naming and organization requirements. See Naming & Organizing Your Media for details.
Edit: If you do rename files and folders, it is recommended that you Plex Dance the movie/TV Show/etc. This procedure removes old metadata and XML information from the Plex database. It can help when Plex has trouble identifying and matching media.
