I have an iPhone 6 that is passed around to people who travel on behalf of our school. I just received it back from someone and wiped it out. Now during the setup at the Remote Management screen, it says the configuration could not be downloaded. Cancelled. It was originally enrolled in DEP with Apple Configurator 2 and added to Pre-Stage Enrollment with no problem. Is this a certificate issue?
We had 25 iPads to be imaged over this summer waiting in their boxes. Let DEP cert expire (do to a failed renewal attempt). Eventually got it back up (downloaded JSS public cert, uploaded to MDM server and downloaded/uploaded token to JSS).
But all of my fresh iPads are getting the same Remote Management issue... could not download... canceled.
I've wiped them via recovery mode in iTunes, re added the serials to Apple School manager, same thing.
Interesting part is Apple Configurator 2 also fails with a similar network issue so clearly I've got something off.
We've also just come from jamf-pro 10.8 to 10.13 to 10.14, and I've heard there were some big changes with DEP.
I've got an open ticket and will update you with what I find.