We occasionally have machines that even though they are configured and assigned in Apple Business Manager and jamf prestage enrollment, they don't trigger the DEP screen. Sometimes we can click the back button and go back to the beginning of the setup wizard and then go through it again and it will then trigger, but a decent percentage it will not.
Any thoughts on what to do in those instances?
If the Mac gets a enrollment profile, it will use that, and NOT ask again (seen that when I change the prestage assignment too late).
Common solution is to erase-install to try again.
A second troubleshooting step is to finish the Setup Assistant, and run
sudo profiles show -type enrollment. That should show what Apple thinks is the current enrollmentprofile for this serial number.
I have seen issues on network with intermittent access resulting in the same behaviour. I suspect the request for enrollment profile is not re-sent by the setup assistant.
A recent video on macadmins slack @yohan demoed on feb5 in #catalina how to reset without erase-installing, but it looked not easy. I hope the link works