Let’s see if log files show anything.
Please do this with minimal other activity on the server - no streaming, adding other content, etc. It does not hurt anything, but the extra activity makes the log files more difficult to read.
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Configure your system for debug level logs.
Settings → Server_Name → General
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Restart Plex Media Server.
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Wait 2 - 3 minutes for Plex to fully start.
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Add a Season folder for the Brooklyn Nine-Nine episodes.
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Plex Dance the Show.
Perform all the steps, in order. -
If the show/episodes still do not appear,
a) Wait 2 - 3 minutes for Plex to log everything.
b) Pull server logs: Settings → Troubleshooting
c) Upload the entire ZIP file to the thread.
FWIW, this works on my Plex server: