Was able to do a bit more testing today, It seems to be definitely only when the subs are burned in. As switching my plex web player settings to “Only Image Formats”:
Results in the subtitles showing without issue:
However this seems to have the side effect of causing playback failures and rendering issues for more complex subtitles that worked fine with the “automatic” burn in setting:
The following plays for a few seconds before crashing and seems to have the wrong font applied:
When it looks fine and plays back perfectly fine with the burn in set to “Automatic”:
I can also do any more testing if needed