Will the fact that Plex doesn’t discover MKV files with long filenames ever get fixed, I love Plex but this is so annoying!
I’ve just spent some time searching for posts about this issue but couldn’t find any.
Would you mind sharing some more details?
e.g. what version of Windows, what file system, what version of Plex Media Server, an example path (full path if possible)… and maybe an example of a path/filename that’s working
Does enabling longs paths in the registry help? If not, does prefixing your library paths in Plex with \\?\ work (mentioned in that same article)?
Outside of that, specific examples of paths that do/don’t work would be helpful as Tom mentioned.
I’m on Windows 11, but 10 had the same issue.
Media server is at 1.32.7.7621 but previous versions had the same problem.
I should check at how many characters Plex starts to find the file exactly but I can say that for example a filename with 38 won’t get discovered and 12 will.
You must not only consider the file name but also the length of the name of all folders and subfolders, from the root of the drive on.
Sometimes you can save quite a lot of characters if you keep the folder hierachies relatively flat and the folder names not too verbose.
I think I found the issue, the file has “S01E01” in it, if I change it to “S 01 E 01” Plex is able to find it.
The pattern S01E01 is typical for a tv show episode.
If you add it into a Plex library that is not of the type “TV show”, it will be ignored. (And the other way around as well.)
I see, all my files are in the same directory so I need to rename or move them for Plex to find them.
Yes, there are some basic organizational requirements, particularly for tv shows.
OK, I’ve added the same direcory as type tv-show, now everything works as I want it, thanks!
After all these years of renaming files 
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