I have a similar problem. However, my MKVs stutter terribly when I try and play them through the desktop web app, almost like a slideshow. If I try and force transcoding, I get the exact same problem as you about 50% of the time… i.e. it just hangs and won’t play. The other 50% of the time it works fine. Playing it on the PMP through a phone, tablet or Fire TV stick works flawlessly. Just the desktop app which is annoying because sometimes the kids watch their stuff on a computer.
Have you tried the Plex for Desktop apps or Plex Media Player?
These are much more capable of playing media than the default web player in a browser.
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