iCloud Data Isn't Syncing

[chorstman]

Over the last 2 weeks several of our managed iPad have received the following message:  "Some icloud data isn't syncing."  When it is selected the message reads: "Your end to end encryption data stored in iCloud can't be accessed...."  There is an option to "Resume Syncing."   When it is selected the wheel spins and nothing happens.  The same message is still there. 

I tried removing the device from the static group so that I could verify their account information, but that didn't take care of it either.  Any suggestions would be greatly appreciated.

[AJPinto]

Put a Mac on the same network as the iPads and run the Mac Evaluation Utility from Apple Seed for IT. My money is you guys are steering SSL traffic and its catching something with Apples traffic that Apple does not like.

If you don't have access to Apple Seed for IT, you can manually check all the hosts using this document below. 

Use Apple products on enterprise networks - Apple Support