Server Version#: 1.30.1.2115-81e1fc3f
Player Version#: N/A
Well, I’ve searched several topics related to Plex displaying the wrong file, but nothing I’ve read so far handles my particular situation.
I’ve ripped my Star Trek Original Series (the remastered ones with new effects), and included the specials that were included on those disks. None of the specials is listed at thetvdb.com, so I used a numbering system that I’ve used for other TV series with success (S00E401-S00E500 is the range that I use for these types of extras).
As you know, Plex will grab a frame from the video file to use as a de-facto thumbnail for an episode if there isn’t one available for download. All the files in my Specials directory are displaying an appropriate thumbnail in Plex - nothing out of the ordinary. However, no matter which episode I’ve got selected in the Specials section, it insists on playing S01E01 (The Man Trap).
To pick an example, I selected one of the specials I want to view. When I select the option to show the file info, it shows this:
W:\Media\TV Shows\Star Trek\Specials\Star Trek - S00E401 - A Star Trek Collector’s Dream Come True.mp4
The metadata for the episode is here:
metadata_xml.txt (2.8 KB)
To the best of my knowledge, that’s correct naming convention for Plex for a TV show, so I can’t see what’s wrong. It doesn’t matter what episode I select, what ends up being shown to me is the file contents located at:
W:\Media\TV Shows\Star Trek\Season 1\Star Trek - S01E01 - The Man Trap.mkv
As a test, I went to go actually watch that episode, and it shows that episode. 
Before someone suggest it: I’ve already done the Plex Dance, and it hasn’t helped.
I shut down the server, restarted, and tried displaying the special episode that I’m using for an example here to get a clean log file, which is attached. Any help would be appreciated - I’m losing what little hair I have left and just can’t figure out why this $#@!ing thing is doing this to me… 
Plex Media Server.log (117.4 KB)