Added Macbook to ABM via Apple Configurator 2 but does not connect to Jamf server

[MerrillM]

We were testing our Apple Business Manager and Apple Configurator 2 enrollment.  We have a few MacBooks that were not added to ABM when they were purchased and need to be added via iPhone Apple Configurator2.  I was able to add the macbook into ABM but now when it gets to the Remote Management screen it gives an error stating  "Enrolling with management server failed. unable to connect to the MDM server for your organization. "
Usually when we enroll a new mac and is on ABM this section has no issues connecting.  PreStage enrollment seems to be setup properly and never had an issue.  Is there a difference for the remote enrollment when the device was enrolled into ABM using Apple Configurator2?  Is this something to check on Jamf Pro or on ABM side?

[morgan-ai]

Check in ABM to confirm that the added devices were assigned to the MDM server - I've found that when I add devices via Configurator, they don't follow the default MDM assignments. 

business.apple.com > Devices > Locate Device > Edit MDM Server (along the top). Then wait a few min after you update the assignment. 

[RobinJJ]

I searched a loooong time for this answer as we added all of our Mac fleet this way.

It's in a small cursive text on Apples website. 

When adding device with Apple Configurator for iPhone, make sure you DO NOT turn off OR restart the machine until you see that it is assigned in ABM and in the Jamf Prestage. When you see that it is assigned in the Prestage, feel free to restart the Mac that you just added.

[Badger]

It was disappointing to see that others have reported this error in other threads but no one seemed to definitively solve it. Reading things like - "reinstall MacOS" struck me as awfully "IT Crowd" type solutions. (Plus, it didn't solve the problem for me :) ) https://www.youtube.com/watch?v=nn2FB1P_Mn8
Here's what I worked out with the help of an excelllent Jamf Support Agent named Brandon. (but it's pretty much what Naisu noted on 10-25-22)

I was experiencing the practically useless-in-detail "Enrollment with MDM Server Failed" on a number of modern Macs (M2, M1 and Intel 2020) runnning Monterey.

What Brandon brought to my attention is the Scope tab of the PreStage Enrollments menu in the JamfPro dashboard.

After scanning the Mac with my iOS device/Configurator and verifying the serial appeared in my ABM account AND assigned to my Jamf MDM (this did not happen automatically for me despite this being my ONLY MDM server), we noted that it took about 3-5 minutes for the Jamf Device Assignment Status to update from "Assigned - Pending Sync" to simply "Assigned".

Running the Mac setup manager BEFORE that status updated resulted in a failure that would never go away (At least I never found a solution for it)

BUT waiting (to go past Wifi Network selection in Apple Setup Manager) to trigger the MDM check until the Mac in question had first settled down into the Assigned status resulted in NOT seeing the error message -- instead being shown the enrollment screen (in my case an Okta login)

In order to 'clear' the state, I needed to reset the Mac. To do this in the most expeditious manner, we aimed to just factory reset from within MacOS.

I unassigned the Mac in Jamf Pro. This resulted in Jamf 'rejecting' the Mac when it reached out in Setup Manager to use MDM and instead allowed the OS to proceed in normal retail setup after which I could perform a factory settings reset https://support.apple.com/en-us/HT212749 -- THEN after returning the Mac to 'assigned' in Jamf pre-enrollment the error no longer was display and successful Jamf enrollment followed.

I _wish_ we could better clear (or even see) whatever is getting cached without having to reinstall the entire OS / factory settings reset. There may yet be better solutions, but I was fully unaware of this Assigning - Waiting for Sync period in the Prestage Enrollments / Scope area in Jamf and feel much more empowered now.

Hopefully this is helpful to others who come here with the same problem.