Does plex have an issue with certain file types streaming to xbox one?
What exactly do you mean?
Basically the Xbox should play everything. If it does not support the format natively, Plex Media Server will transcode the file into a format Xbox can understand.
I myself had 1 or 2 MKV´s files which did not work, because there was something wrong within the file and also the First Party Media Player thought it could play them and crashed … (But these are isolated incidents)
If you have media that just produces a black screen when you try to Direct Play it then we would like to get a sample please! We automatically determine when a file needs to be remuxed/transcoded but there are some edge case odd files that can produce playback issues.
so it’s an MKV file but it gives me an error when I try to play it I’ve tried other files and they work fine. I also tried the same file on my laptop and iphone with no issues. I will post error from xbox when I’m home
A sample will definitely help the developers try and figure out what is causing the video player to choke while direct playing these files.
In the mean time I found that if I disable direct play from the settings menu all of my files that were unable to play will begin working. It does use more resources on the server because the will then need to Direct Stream/Transcode, but at least they don’t error out.
I also will post then when I encounter a file again. I know it was 2 episodes of “The Good Wife” but not which … and I don´t want to try every episode again 
We certainly have had edge cases with supposedly supported MKV files that cause freezing/black screen on playback. We’re looking into how to address this better. For now, if you bump into a case where Direct Play isn’t, er, playing directly, try going to the settings and turn off ‘Enable Direct Play’ and see if remuxing or transcoding the content works. Not ideal, but would be useful (along with sample and codec details) for us.
@moussa.uk I’ve got an mkv file that produces a black screen when I try to Direct Play. I’d like to send a sample, but the file is 850 MB. Where can I upload the sample?