Conversion failed. The transcoder exited due to an error

The problem is still subtitles related.

Using Plex Web, could you locate these media files in the library and get me the media info xml

/storage/NAS/video/Films/HD MOVIES/Deadpool.2.2018.The.Super.Duper.Cut.Multi.1080p.Blu-ray.x264.DD.5.1-DTOne.mkv

and
/storage/NAS/video/Series/Jack Ryan/S01/Tom.Clancys.Jack.Ryan.S01E05.REAL.PROPER.1080p.WEB.H264-BATV.mkv
See https://support.plex.tv/articles/201998867-investigate-media-information-and-formats/

Might need to go through the Plex Dance sequence having changed the subtitles options

See The Plex Dance ™