Server Version#: 4.132.2
Player Version#: 7.23 Build 6
TCL Roku TV
Not sure if anyone else is having this issue, but when playing things from the TV app, it does not queue episodes in the correct order. Normally, in the web app and phone app, it queues by release date, so specials and what not will appear where they are supposed to, but in the TV app, it only goes season by season, so you miss specials that are supposed to be watched after specific episodes.
The only way to get around this for now is to cast to your TV app from your phone or computer, then play things from there. This is a bit of a pain though, so I hope Plex can address this bug in a future release.