Okay, this is a minor issue. But I’m a bit OCD and it’s something that pisses me off.
I have my season folders for shows as follows:
Season 0
Season 1
Season 2
etc...
Season 0 is the “specials” season.
I have recently started dropping local image files into the directories so that I can auto-populate poster images:
poster.jpg
season specials.jpg
season 1.jpg
season 2.jpg
etc...
What you’ll notice above is that the poster for season 0 is not season 0.jpg. It has to be season specials.jpg. Again, this is a minor issue… but it’s really bugging me. I should be able to name the image season 0.jpg.
In addition to your media naming not being exactly what plex wants your local artwork does not match the plex recommendations. This doc should help you. Local Media Assets - TV Shows | Plex Support.
Local assets are awesome for those of us who care about such things but plex is somewhat unforgiving if your stuff is not named correctly. Best to follow their naming rules or it’ll just not work correctly.