Server Version#: FreeNas 11.1
Player Version#: 3.79.0
When I go into the web app on the plex website and try to play an mkv file, it says “playing this type of media is unsupported.” I have another server I can connect to and it’s doing the same thing.
Do you experience the same behavior when accessing those videos from a different client or browser?
I’ve just tested it and my MKV played fine in Safari on iOS 12
Hi thank you for the reply, I have. I tried using other browsers on my phone, but it does the same thing. Chrome, Firefox and internet explorer. I’m running an older version of iOS though so I think my problem might be that. Version 10.3. I never upgraded to a new version because I didn’t want my iPhone 6s to slow down. If I try it from an Mac it works. Just not iOS. Windows works as well.
I also noticed recently that none of my iOS 12.1 devices (iPad and iPhone) can playback mkv files anymore from Safari web browser.
I downloaded Chrome but that didn’t help.
I noticed MP4 video files play fine, unfortunately my library consists of 99,9% mkv files so that doesn’t help me much 
Playing mkv videos has worked just fine on iOS devices previously.
I am currently running Plex server 1.14.1.5488.
Can anyone confirm the same playback issue on iOS devices?
Yes I’m having the same issue. Unfortunately almost my whole library consists of mkv files. I’ve put a lot of work and time into my library so I really don’t want to redo everything. I noticed this error occurred when Plex discontinued its cloud service. I’ve tried almost everything to resolve this issue in the advanced settings menu but now since you said you’re having issues on IOS 12.1 then I’m thinking it’s an issue with plex. I’m not sure how to contact them to look into this either, so I don’t know what to do. You can download the app and pay one time 5 dollar fee to play mkv files but I didn’t want to do that.
I have a Lifetime Plex Pass so I have the Plex app on my devices but I have some iOS friends on my server that have playback issues. Last time I checked, it was working fine on iOS, but not anymore.
I would like to know if Plex has intentionally stopped the possibility of streaming mkv videos on iOS devices.
I am also suprised by the comment of @tom80H who does not seem to have issues streaming mkv videos on iOS 12 devices. That is surprising, but also gives me hope this can be fixed…
@tom80H: Have you done something special in order to stream mkv videos on your iOS devices?
@tom80H, I was able to replicate the error “playing this type of media is unsupported” right off the bat using https://app.plex.tv/desktop on Safari on my iPhone X running iOS 12.1.2
The same video works fine from ATV plex client, iOS plex client, and Mojave (both PMP and the hosted web client).
I’m somewhat surprised that the web client on iOS/Safari works for you…
@tom80H: any input from your side as a moderator?
Any input or information about mkv playback on iOS 12.x devices would be greatly appreciated.
Just read this post: Web Client error IOS devices
Finally a Plex employee stepped forward and mentioned they’re aware of this issue and are working on a fix.
This issue is finally solved in Plex Web 3.91.0:
Fixed ‘Streaming this media is unsupported’ error in iOS Safari
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