Plex Documentation → Your Media → Naming & Organizing Your TV Show Files
Season folders should be named Season XX, not Show Name - Season X.
Try renaming the season folder to Season 06 and correct other seasons if applicable. Plex Dance the season (or entire show) if needed.
/Outrageous Fortune (2005)/Season 06/Outrageous Fortune (2005) s06e14.ext
PMS 1.25.8.5663, Synology DS918+
Using a JellyFish test file in place of actual episode (hence the 30 second duration):
