Run this on your DEP testing computer, it'll bring it back to a state that will kick off DEP on reboot. Also, VMs will be your friend as well

!/bin/sh

Remove .AppleSetupDone Allows the Setup Assistant to show again

sudo rm /var/db/.AppleSetupDone

Remove JAMF Binaries and Software

sudo jamf removeFramework

Remove any lasting Configuration Profiles

sudo rm -rf /var/db/ConfigurationProfiles

Remove apds.keychain This is on recommendation of Apple. Seems to have some push cert related data in it

sudo rm /Library/Keychains/apsd.keychain

So how do you get the VM's into your Apple Deployment environment so jamf can see it as a Mac ready for DEP enrollment?

If you read the post it explains how to build the vm for testing with DEP ;)

Basically you spoof the serial # of your VM with a serial # from actual hardware.

+1 @rderewianko. Doing the same thing here!

I tried and got this error

Does this process still work with Jamf 10.21 and Catalina 10.15.4? I do not trigger Remote Management in a VMware VM, but the physical machine with the same serial does trigger.

@davidi4 The serial numberand model number must be correct, and you have to set them before doing the macOS install on the VM. See this thread for more discussion: Enrolling OSX virtual machine into JSS - Issues

There is additional information in Traveling Tech Guy's article, following his steps actually worked for me - I believe the addition of the reflectHost = FALSE lines were key:

serialNumber.reflectHost = "FALSE"
serialNumber = "C02NXXXXXXX"
hw.model.reflectHost = "FALSE"
hw.model = "MacXXXXX#,1"
smbios.reflectHost = "FALSE"

https://travellingtechguy.eu/vmware-dep/

I build and test in a VM, but before final sign-off run on actual hardware. We've collected retired hardware and on occasion have an opportunity to intercept new gear before it gets to the user. Gives us a variety of actual hardware to test from. We always try to test at least one model of laptop and a later model iMac.