Plex not recognizing valid files in the library as recorded from the DVR

My husband’s wanted to keep DVR recordings ‘separate’ from So I created a separate folder on my drive for DVR shows (labeled DVR) and another for DVR movies, separate from the Movies and TV Shows folder, and we have created libraries specifically for those folders. This has produced some issues.
First, here is the problem directory. Everything seems to record and go into their proper folders just fine. The naming schema, as far as I understand it, should work. Every other show we’ve recorded, from its own folder with the same naming schema, works fine.

But from the Plex interface, this is all we see in that directory, even after multiple library scans:

Note that Supernatural does not show up AT ALL. I think this may be related to the fact that our TV Shows library (a completely separate library pointed at a completed different directory on the hard drive) also has Supernatural in it, though a completely different season. I base this on this weirdness:

Note how the episode number in the corner of the show image is 24, while the episode number in the corner of the only existing season is 23? I think the media server is getting super confused because it knows (from the metadata) it’s dealing with different episodes of the same show, and it’s throwing a fit about them being in different libraries and directories. (And no, adding the DVR directory to the TV Shows library for scanning doesn’t fix the problem).

Any ideas?

I should also note that in the TV shows directory, it says that Supernatural has 2 seasons, but as you can see here, it is only recognizing 1 season. Which seems to indicate there is a hidden, second season with only 1 episode (because of the 24 instead of 23 episode count), which is how many I have in the DVR library that are not showing up at all.

More notes on further testing:

  • completely moved the files from the DVR folder to the TV Shows folder. Still won’t recognize the episode or season.
  • Converted the ts file to mkv (which was able to properly store the CCs in usable form. Hooray!). Still won’t recognize the episode or season.
  • tweaked the file name to EXACTLY match the format used in the already existing season (DVR stores it and adds the year of series starting and episode title. I typically just use show name and s##e##.extension). Still won’t recognize episode or season.
  • tested the file in VLC. Works perfectly.
  • Scanned library files (a dozen times), refreshed metadata, and analyzed the library, multiple times. Still won’t recognize episode or season.
  • rebooted machine server is on. Still won’t recognize episode or season.
  • told TV Shows library to not scan the DVR folder. Still won’t recognize episode or season.

I’m at my wit’s end. This makes NO sense. It’s basically not even the same file that was recorded by the DVR anymore, since it’s been renamed and converted and moved, but Plex absolutely refuses to acknowledge the existence of that episode or season aside from the numbers (from TV Shows, the thumbnail of the show says there are 2 seasons, though when you click on the show there is only 1, and the tiny number in the corner of the thumbnail of the show when in the show says there are 24 episodes, though the only season it shows has only 23 episodes). Someone please, PLEASE help me!