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 ™