Cannot seem to get a TV show recognised

That step is important. You do not need to delete permissions, just re-apply with the correct settings.

Not sure why the shows are taking so long to appear. A manual scan of the library should pick them up immediately.

If you like, we can take a look at the Plex log files and see if they show anything.

  1. Ensure Plex Media Server is configured for debug, not verbose, level server logs (Settings → Server_Name → General + Show Advanced).

  2. In Settings → Library, enable Scan my library automatically (Plex will scan the libraries when it starts. It also adds some additional info to the log files).

  3. In Synology Package Center, stop Plex, wait ~20 seconds, start Plex (this makes sure the startup sequence is logged).

  4. Wait 3 - 4 minutes for Plex to fully start & log the startup sequence.

  5. Plex Dance Boardwalk Empire.

  6. If the show still does not appear, pull and post a set of server log files (Settings → Troubleshooting). Upload the full zip file to the thread (drag it into the message window and wait for the upload to complete).