Won't play MKVs all the way through anymore

Cliffs at bottom.

I’ve had Plex for months without an issue. I have a Asus Windows 10 laptop with an i5, 4gb ram etc. I always have used my PS4 for viewing my files. Sometimes PS3, and after I ran into the problem I paid $5 for unlimited access on iOS devices and ran into the same problem on my iPad Pro 10" I just updated my Plex server software to Version 1.1.4.2757 All my files are on External hard drives linked through a USB hub to my Asus laptop that I use as a server. Then a cat5 cable is ran directly from the laptop to my Airport Extreme. PS4 has a wired connection too. Again, I’ve been using this setup for several months with no issue. It still plays older/most files without a problem. But two wrestling shows and Back In Time wont play all the way through. Trying to figure out what I can do to fix it. I’m probably nowhere near as smart as any of you guys and am newish to this stuff. I used to just use things like a WDTV, XBMC for a bit or just a HDMI cable to my laptop while playing in VLC and extending my desktop to the TV.

It started when I tried to download a couple MKV files and they stopped playing a few minutes in. Then I downloaded Back In Time and it stopped playing about 1:04 in. Wont play after that at all. I can start it over and slowly skip to about the same point, and then it just goes black and tries to load it, but it never works . When I try to resume from last played time it says: “There was a problem playing this item.” “The Video did not start playing in time.”

Cliffs: Stops at certain points on newer MKV files, always gets stuck at that same spot on that file whether its 5, 10 or 65 mins in.
Using a Win 10 laptop, newest Plex software. Using a PS4 to view, same error with an iPad using the Plex app.

Please help guys!! Thank you SO much. IF there is any other info I can give you guys at all, let me know. :slight_smile:

Should I use Handbrake to reencode the files? In as a MKV out as a MKV?

Sorry its been a while lol

Any update on this? Is there an easy way to fix the files?

Thanks in advance for any help.