Has anyone figured out a way to do this? I'd like to remotely add videos from my PC to the Shield and then watch them on a mobile device. Only issue im having is the server won't display the video until I go into the Shield and physically update library. won't be due to do since im not near the Shield. Looks like auto library update is an option on the windows Plex server. Can't find it here.
CouchPotato (movies) and Sonarr (tv) can both push notifications to Plex Servers:
https://forums.plex.tv/discussion/147603/notify-plex-of-downloads-via-couchpotato
https://github.com/Sonarr/Sonarr/wiki/Supported-Notifications
Haven't tried setting this up on Shield yet but hopefully it works as expected.