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It's been a while but I finally got a chance to take a look at this issue again. The mediainfo tool didn't show any problems with the files that cannot be played by Windows 10 (either by the Movies & TV app or by Plex). For reference, I ensured that the blu ray drive could still play the blu ray...

The compression of the file failed; Handbrake crashed during the process leaving an incomplete m4v file. This has been consistent with my recent rips as well. Because of the crash the Handbrake log file is incomplete so I'm not sure why it crashed. Is there any way to examine the structure of mkv fi...

The VLC video player does work, thank you. Oddly enough other MKV files on my system are recognized as video files by Windows and play in the Movies & TV app. They are ones that I compressed using handbrake however. I'll try compressing and see if that works.

I've ripped most of my Blu-ray collection to a hard drive but recently started having trouble. Every Blu-ray I try rips without error but the resulting MKV file is unplayable. I've tried blu-rays from several manufacturers to be certain (Moana, Fantastic Beasts and Where to Find Them, The Thing, etc...