Server Version#: 1.27.1.5898
Player Version#: 1.19.1.3076 (HTPC)
I live in a hearing impaired household, so we have subtitles and captioning turned on by default.
When playing a DVR recording in TV Shows, we have to turn the captioning OFF and ON again to get it to display each time we start watching or resuming playback. (I remember seeing this same problem in other Players in the past).
Captions for Live TV (OTA) seem to work okay, as do local Movies subtitles, although I need to do a little more testing on some of the other Plex streaming services.