Why do subtitles show for a while and then stop?

I have been having problems with the subtitles stop showing. I have both internal PGS and external srt and synced. They will play for a while and then stop. I have to turn subtitles off and then on multiple times throughout which is annoying. I primarily use MKV files but it seems to happen with avi and mp4. I am using the windows plex server.

Thank you err…trumpy (seriously? You seem sane so…I guess you’re not related ;-)). I rarely use subtitles but have had a need for them recently and having to flip them on/off every ten seconds is an even worse problem than the PS4 Plex client crashing all the time.