Are you using mp4 file containers?
Rippers and encoders are often embedding nonsensical Title tags, which can severely disturb Plex’s matching, unless you tell Plex to disregard them.
Go to
- Settings - Server - Agents - Shows - TheTVDB
In there, grab the line ‘Local Media Assets’ with your mouse and drag it downwards, so it ends up being at the bottom of the stack of active agents.
Repeat the same under
- Settings - Server - Agents - Shows - TheMovieDatabase
- Settings - Server - Agents - Movies - Plex Movie
- Settings - Server - Agents - Movies - TheMovieDatabase
Make sure your files are also in the recommended folder structure for tv shows.
https://support.plex.tv/articles/200220687-naming-series-season-based-tv-shows/
After doing the above, perform the Plex Dance with the whole show.