Movie Playlist Rarely plays next in queue

I’ve been working on trying to figure out what is going on with this for nearly a year now. I have a movie playlist that I want to play next in queue when the first movie is done. Sometimes this works, but most of the time it doesn’t.

To make matters worse, if I start the playlist then forward the movie to the end of the show the next movie will always play. It seems I have to watch the movie all the way through before it will work or not.

I’m on the most current version of Plex (1.8.3) and have tried two different physical servers and am operating on a virtual service (win 7) right now.

I’ve tried to start the playlist from a computer and have run into the same issues as I have on Android. Anyone know what may be going on?

Why did I buy the product when there’s no support?