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We are switching from managing iPads through Jamf Pro to Jamf School, and I was wondering if there'd be a way to automate the re-enrollment without wiping and re-enrolling through DEP?

I'd definitely want it as a supervised enrollment, but not the end of the world to have to just push out a wipe and re-enroll with DEP.

If you're switching MDMs then you need to wipe the device and re-enrol it to the new MDM.