Plex Playing the Wrong Episodes

Plex Players Desktop Players
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Plex is playing a different episode when I attempt to watch certain episodes of the series Monogatari(2009). This doesn’t look like an issue with the file naming. It has full metadata for both episodes, but when I click on one, I get the other. This only seems to happen with the specials. S00E03-05 all play S03E01.
S00E10-18 all play S04E01.
S00E21-32 all play S00E19.
S00E34-38 all play S00E33.
S00E 2, 19, 20, 33 play correctly.

The odd thing about this is that the affected episodes are grouped by series ark, they have similar names. I.E. S00E03-5 are all named Tsubasa Family parts 1-4.

I can reproduce this 100% of the time on Plex for Mac and Plex Web by going to the series and clicking play on any of the above episodes. This issue does not occur on my Roku smart TV. I attached my naming scheme, and also did a plex dance for good measure.

Server Version#: 1.22.0.4163
Player Version#: 1.28.0.1681-cc6e807c
dir.txt (7.8 KB)

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Have the same issue without having S00E15-S0018, S00E20-S00E38, Season 4 and Season 5 inside my Folders.
S00E10-14 plays in my case S00E02 and loads playlist which skips to S00E10.
Observed it on Windows and Chrome player. The Shield TV and Android player is working correctly.

Server Version 1.22.0.4163 (Shield TV)
Player Version Version 1.22.0.4163 (Windows)
Player Version Version Version 4.53.0 (Chrome)

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