Anybody know why this is happening?

Plex Media Server Desktops & Laptops
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2

It happened because your files are not named or organized per Plex recommendations.

See Naming ‘Series’ & ‘Season’ Based TV Shows.

The correct format is:

  /TV Shows
   /American Dad
      /Season 11
         American Dad - s11e08.m4v
         American Dad - s11e09 - Stanny Tendergrass.m4v

To fix, you’ll need to rename the files and perform the Plex Dance.

  • move all files for the media items out of the directory your Library is looking at so Plex does not “see” them anymore
  • update library (scan for media items)
  • empty trash
  • clean bundles
  • Fix naming and organization, then move files back to library
  • update library (scan for media items)

Plex is very picky about names & structure when it comes to TV shows. You might get lucky with iTunes formatting (key word = lucky). Using the downloaded files without cleaning up the names is asking for failure.

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