MasterClass metadata

Plex Media Server
,
2

Are you talking about this show? MasterClass - TheTVDB.com
If so, the key elements are

  1. follow the recommended naming scheme very closely
  2. add the TVDB ID number to the folder name
  3. set the Episode Ordering of this show in Plex to “TheTVDB (Aired)”
/TV shows <-- Plex library pointed to this folder
   /MasterClass {tvdb-362158}
      /Season 01 [James Patterson Teaches Writing]
         MasterClass - s01e01 - Introduction.mp4
         MasterClass - s01e02 - Passion  Habit.mp4
         MasterClass - s01e03 - Raw Ideas.mp4
         ...
      /Season 02 [Usher Teaches The Art of Performance]
         MasterClass - s02e01 - Introduction.mp4
         MasterClass - s02e02 - Getting Started.mp4
         MasterClass - s02e03 - Gathering Inspiration.mp4
         ...
      ...

The reason that the season titles are in square brackets is so that they don’t confuse the matching algorithm of Plex.
Plex will not fetch any metadata from the file and folder names anyway. They serve only to provide matching hints.

After your previous naming experiments, it might be necessary to perform the Plex Dance, to clear any mismatches associated with the files from your server database.

There is another show named Masterclass: Masterclass (TV Series 2010-2014) — The Movie Database (TMDB)
In which case the folder name changes to this:

/TV shows <-- Plex library pointed to this folder
   /Masterclass {tmdb-47075}

And the Episode Ordering needs to be set to “The Movie Database (Aired)”.