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We have been using locally hosted Jamf Pro connected to Apple School Manager with locally hosted Apple Caching to support our 1,000+ iPads and 75 Mac OS devices.

A local vendor has a good price for managing a migration. I can see some cloud-based advantages should we go to distance learning again. If anyone else is operating in the cloud today some questions.
1) How has local updating run - are on site devices still using local caching servers
2) For remote devices - are they receiving updates from your internal caching servers or direct from Apple?
3) Any adventures during migration that caused problems?
4) Any issues with Shared iPads?
5) Did you have to re-enroll if the same URL was used?

  1. We use content cache's on sites that have other Macs (iMac lab for example) but have also set up a JamfShare on our existing Windows DP's for our Macs to pull locally from (it was much easier to set up HTTP on existing Windows Servers than macOS). This is sorted by Network Segments as unfortunately you can't set the Cloud DP as a failover.
  2. Direct from Apple as they'd need the VPN otherwise.
  3. You have to wipe iOS devices to re-enrol them (they left that part out until we were committed). macOS was done by policy and was easy. Also if you change the management account on re-enrolment the Mac won't pull from the CloudDP (took a while to problem solve that one).
  4. N/A
  5. It's a new URL https://xxxxx.jamfcloud.com unless you pay the extra $$$ for your own site. The issue with getting users to re-enrol iOS devices is they'll hit a "a profile containing an MDM payload must be removable" message and go no further.

Overall we paid for the migration tech from Jamf. They were obviously learning as you could hear the instructor over the call, but it was thorough and went pretty well. Certainly worth doing for off-site management though.

Thanks for the insights!

Pretty sure you can keep the same URL. You just have to point a CNAME for your current URL to your Jamf Cloud address. Make sure you do it in your external and internal DNS. Your database moves right over during the migration.

Also you and Jamf can probably handle the migration all by yourself.

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