This is a weird one. We're using iCloud to backup a user's iPhone (unenrolled and unsupervised). From there, we're trying to then enroll/supervise the device into both DEP and Meraki (via Apple Configurator), which works successfully. However, when restoring from iCloud backup, this appears to remove the supervision. The device shows up in Systems Manager and on Apple Business Manager (under the MDM server, "Devices added by Apple Configurator 2"), but the iPhone shows no profiles installed on it, and Apple Configurator does not say the device is supervised.
Browsing around online, there seems to be some kind of way around this (see here: https://www.jamf.com/jamf-nation/discussions/24019/backup-devices-before-wiping-and-enrolling-throug...), but I can't quite figure out how to get this to work.