I recently upgraded from a old Roku 2nd gen, to a Nvidia Shield TV Pro 2019 model. Works great with Plex, but last night, I went to continue watching an Anime with subtitles in ASS format, only to be prompted with “An error occurred while attempting to play this video. Please check your connection and try again.”
I watched over 20 episodes of the show in question with subtitles on, with no issues. Now for some reason, I can’t even play the episodes I already watch (which I obviously can confirm, worked previously). I tested the media files on the server with VLC, with iOS, Chrome web player and I also installed VLC player on my Shield TV and tried the media files. All played with subtitles just fine. This seems to be only affecting media with ASS type subtitles, hosted by Plex. PGS and all other subtitle codecs work fine still. I also had my friend test it on a Android based smart phone, which worked fine as well.
My server is hosted on a HP Blade Server with plenty of transcoding power (I’ve been using plex going on over 8 years now), I’ve restarted the Plex service (running as service in Windows) and I’ve restarted the Plex Host to no avail.
Server Version: Version 1.24.3.5033 - Though is was not recently updated, I’ve been using this version since it’s release a few weeks ago, with no issues. This seems to have just started last night for no reason.
Log files Plex Media Server.log (1.5 MB)
Note, these log files were pull IMMEDIATELY after I attempt playback and received the error message. So anything relevant should be at the very bottom of the log file. I tried to make it as easy as possible 
A line on the log file to reference is “Oct 13, 2021 22:24:32.112 [2996] WARN - [Transcode] Got a request to stop a transcode session without a valid session GUID.” and the barrage of errors/warning above it.
Any help is appreciated as always!