I’ve never been able to get these to work… on any iOS device it just closes the play window within a few seconds, and if I try to play them from the web app it just sits there and spins forever and never plays. What could be the problem?
Never mind Figured it out…
From the Web app i clicked download video (trailer in this instance) it redirected me to an XML page with an error “The ‘e’ parameter containing the expiration date (1505878966) is earlier than the current GMT time (1505879525). The link has expired”
This made me think as SSL has issues when the time is wrong on the host and server machines. Maybe plex does something similar when you click play on an extra it as expires the content you want to watch after a certain about of time. I checked my servers time and sure enough it was off by about 14min. I re-synced the time to time.nist.gov and then tried to play the file, and it worked perfectly.
Hopefully anyone else having this issue this will help… Just make sure your time is correct 
