Student Photos on Shared iPad Screens?

[bumbletech]

Right now all of our shared iPads only show a student's initials‚ however the Classroom app will show the student's picture.

I found this guide (http://docs.jamf.com/technical-papers/casper-suite/apple-school-manager/9.92/Prepare_to_Enable_User_Images.html) for doing this (I hope), but I'm a bit lost on the "Establishing Trust Between the JSS and the Web Server" section. Does anyone have a more step by step process for doing this with Server.app on macOS?

[RLR]

I know this is an old thread but did you get an answer to this. I'm currently doing this at the moment and stuck on this bit. The photos are displaying correctly in JSS under the users but the photos are not displaying on the iPads. Must be something to do with this trust setting.