UPDATE 20th of November: Parallels released an update for version 14

https://kb.parallels.com/en/124521
"Resolves an issue with the Apple DEP (Device Enrollment Program) not working in a macOS virtual machine"

CONFIRMED: Works perfectly in Parallels 14.1

In my previous post I discussed the steps to create a VMware Fusion virtual machine, which is behaving like your “automated MDM Enrolment” test device (previously known as “DEP”). While I personally use VMWare, in combination with my ESXI homelab, I promised to post the workflow for “Automated MDM Enrolment and Parallels Desktop” as well.

So I did some testing…

The good news is: it still works on Parallels Desktop 13, even with macOS Mojave.
The “bad” news is: I haven’t succeeded in getting it to work with Parallels Desktop 14. – See update above. I will test and update the blog ASAP.

Here is what I did, as well as the working configuration for Parallels Desktop 13 (confirmed on Version 13.3.2 (43368) with macOS 10.14.1)

Click here for the Tutorial on how to do this on Parallels 13.

I knew it works on Parallels Desktop 13, and while I was reading about people having issues getting it to work in version 14, I still gave it shot. But unfortunately I also ran into multiple unexpected and inconsistent results. Sometimes it detected the Jamf Pro pre-stage but failed to contact the MDM server, sometimes it didn’t detect it at all and setup assistent acted like there was no prestage. Part of the inconsistent results I got is also the fact that sometimes the VM would just fail to contact the MDM server after detecting the pre-stage, while on other runs it ended up being stuck at “Retrieving the activation record”… as said overal some very inconsistent behaviour.

Stuck on “Retrieving activation record’? Sometimes it actually failed and threw an error saying “Unable to Configure Your Mac”.

Or simply… unable to connect to the MDM server…

You would assume network issues, but I can guarantee you this is not the case, as same network and same virtual network settings work fine on Parallels Desktop 13 and VMware Fusion 10/11 (as well as when auto-enrolling physical devices on the same network). I also tried different virtual network settings, such as shared and bridge which all work fine on Parallels Desktop 13… and even tried on other networks and hotspots.

So, I decided to remove PD14, install Parallels Desktop 13 again, and booted the VM I created with Parallels Desktop 14. Guess what? Behaved 100% as expected and enrolled through Automated MDM enrolment without any problems!

The behaviour I’m seeing, makes me think it’s virtual network and/or serial number related, but no idea what’s actually going on… \_(ツ)_/¯ 

The good news is, it works on Parallels Desktop 13, so for now let’s park the Parallels Desktop 14 issue and have a look at how to achieve our goal with version 13.

Tutorial Parallels Desktop 13

Pre-requirements:

  • Parallels Desktop 13 (confirmed on Version 13.3.2 (43368) )
  • macOS installer downloaded from the App Store (confirmed Mojave OK)
  • Serial number of a device which is listed in your Apple School/Business Manager: e.g. C02N49ZVXXXX
  • Model number of the device: e.g. MacBookAir6,1
Note: the screenshots below are made in PD14, but the steps are exactly the same in PD13. Furthermore, the PD14 VM worked in PD13 and enrolled fine through Automated Enrollment / Jamf Pro prestage!
First step, after downloading the macOS installer from the App Store is to create a new VM from “an image file”.

Select your macOS installer or navigate to it manually if Parallels Desktop doesn’t detect it automatically.

Parallels Desktop is going to create a bootable disk image from the installer you selected. Just hit Continue.

Wait…

Give the bootable disk image a name and location.

Customise your VM!

Name your VM but don’t forget to select ” Customize settings before installation”! If not, Parallels Desktop will launch your VM immediately after creating it, and we need to do some changes in the settings  to add the serial number and model for the Automated Enrollment to work!

Do not hit continue!

Click on “Configure” !

Go to Hardware -> Boot Order -> Advanced settings, and add the following Boot flags:

devices.mac_serial=”C02SQWERTYUI”
devices.smbios.serial=”C02SQWERTYUI”
devices.mac_hw_model=”MacBookAir7,1″

(Replace serial number and model identifier with the information of your test device)
UPDATE 16/11/18: do not use ‘devices.mac_serial’ as this is deprecated in favour of ‘devices.smbios.serial’ 

Hit Continue and wait for the VM to boot.

Install macOS as usual…

Just like on VMware Fusion, when you reach the setup assistant, first stop the VM. This to make sure the model identifier and serial number persists. 

Launch the VM and make a snapshot before advancing in the setup assistant. This again to allow you to do multiple enrolment tests in a fast and efficient way!

Once you have your snapshot, continue with the setup assistant…

and there it is! Remote management… with the issues I mentioned on Parallels Desktop 14:

While in PD13 in works fine:

After successfully contacting the MDM server in PD13, theVM nicely follows the Jamf Pro pre-stage… skipping setup assistant items.

Now, what’s actually causing issues in PD14… I don’t know yet, but here are the steps I did to isolate the problem:

  • Run the PD14 VM in PD13: OK
  • Install PD14 on another Mac and create the VM again: FAIL
  • Create the VM from scratch in PD13: OK
  • Run the PD13 VM in PD14: FAIL
  • Try PD14 with High Sierra instead of Mojave: FAIL

If anyone has more luck in getting this to work on Parallels Desktop 14, please let me know what I’m missing but for now I’ll leave it at “it works in PD13″…

Grtz,
TTG

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