Playback has stopped because the connection to the Plex Media Server has been lost

Have been running into this error message a lot lately. Happens when I am playing episodes from a mixed playlist, several different TV shows. It started popping up in after playing several episodes, I was would have to go back to the playlist and pick up where I left off, as retry would not work. Now I get the message after every single episode,
It does not do this when playing a playlist of movies or when playing episodes sequentially from a TV series. It does do it with Smart Playlists.

Any help would be appreciated, as this pretty much breaks Plex for me. Being able to load a bunch of random shows on to a playlist and hit shuffle is our primary usage of Plex.