I have tried removing the files, emptying the trash, then re-adding them with different names. The result is the same. Any new specials that I had will not play. Instead it plays the pilot episode.
No dice, it still malfunctions the same way.
Yes, how do I send those to you privately? I donāt particularly want to post my logs to the public.
I sent the logs in a PM.
Exact same behavior in the new test tv library as well.
\apollo\Media\Test TV Show\
I replicated the problem tv show, with the first episode, along with the first special that plays correctly and then the second that doesnāt (I did not bother copying all the others that do not play correctly as well, nor all the first season episodes, since that would take forever).
May I ask how they are named please?
Iād like to make a quick check here.
The Plex forum had locked me out from replies for 21 hours due to being a new user it said.
Sorry the actual path you were looking for was ā/volume1/Media/TV Showsā
So the files themselves are fine and in the intervening time-out, I did some different tests and was able to narrow down the cause. Having the year in the name or not, did not effect it either way.
If I have a Specials folder that contains some special content that matches to the TVDB and some that doesnāt, it breaks in the above described manner.
I donāt know if this is consistent across all programs or selective, but I definitely happens with Breaking Bad.
When I name my special episodes so that none of them match the TVDB, then plex is happy and will play them correctly.
Iām not sure if the Plex folks will consider this a bug, but I sure do. Given that tons of users, such as myself, have lots of extras from discs, that never aired on tv and will never be included in the TVDB, this is very problematic.
My files that do not match TheTvDb are in the following example format
Breaking Bad - S00E318 - Inside Breaking Bad - The Opening of Season 3.mkv
They are the same as the ones that do match, except that I use a hundreds range episode number to avoid any collision with actual matching ones. In this case all season 3 extras have a 3xx episode number.
Ah ok, thank you. I thought the exras directories were only supported with movies and that TV shows only supported the Specials directory. Is that something that changed in recent months?
Ah ok, that is good to know. Thank you for the information.
I just upgraded to latest version 1.23.2.4625 and guess what: the issue has been fixed!!! Thanks a bunch PLEX for fixing this 
I just upgraded to the latest server version of 1.23.3.4707 and the bug is back. Certain specials are not playing the correct file but instead playing a regular episode of the same series.
Here we go againā¦
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I canāt confirm that; my specials still play as expected with that versionā¦
Was having same issue. Found the āOriginally Availableā date set to 1900-01-01 in the edit screen for the episode. Changed the date to something a bit more reasonable like 2005-01-01 and the special played normally. I was able to reproduce this repeatedly by changing the date to 1900 and then back to a date closer to the present.
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