Windows 10 Subscription Activation Not "stepping-up"

We recently decided to make the switch from KMS to Subscription activation for our E3 users. I've been able to successfully test this in a few different situations when I've run into a roadblock. Due to our size, we will face a struggle forcing everyone to change to their Azure AD creds (name@domain.com), so we intended to run the script Microsoft recommends for manual activation. To do this via SCCM, however, we wanted to set a configuration baseline to remediate any machines that do not make the switch by using powershell. We wrote a script that successfully activates the underlying pro license, but now these machines are not making the "step-up" to enterprise. 

I attempted to run the script MS suggests on each of these machines since, but to no avail. I have also made GPO changes and registry changes suggested on other posts but that also did not work. 

I opened a ticket with MS but they have, so far, only suggested changes that I have already made. Does anyone have any sort of experience with making this change to subscription in an enterprise environment? How does the "step-up" to enterprise occur? I'm struggling to find any sort of information to aid me in troubleshooting where that piece may be failing.