It does seem a bit odd.
Enable Debug Logging: Settings/General
Prepare to download logs and post them when asked: Settings/Troubleshooting
Do this so we can generate some fresh ‘Debug’ logs:
Plex Dance The Show (only one season so let’s start over), half the season at a time and see what happens (your watched state will not be affected):
Pull the Show - scan - empty trash - clean bundles.
Put half the season back - do the last half first - for grins…lol
Note:
I just added another new show - it took 10 minutes to negotiate the artwork and descriptions - a process that is almost always nearly instant. Give it some time.
