My last post was about getting a Windows 11 VM up and running on Apple silicon under UTM; this post was the next phase after I got my VM running where I wanted to license it. Windows licensing, especially for random VMs, is kind of funny these days. Back in the day, if Windows wasn’t licensed then Microsoft wouldn’t let you install any updates. Naturally, there were plenty of people completely undeterred by this who then went around running horribly outdated and unpatched systems just teeming with security vulnerabilities. Microsoft eventually thought better of this and decided to be (arguably) even more annoying by keeping users from customizing the system at all to suit their preference. While that’s undoubtedly super annoying for anyone trying to use a Windows install as their primary system, for one off VMs used to test the occasional thing here or there, is it really that big of a deal?
I would generally say “no” and frequently don’t bother to license that category of VM, especially the ones that I know will be shorter lived (e.g. I use it to make sure something runs on Windows clients periodically throughout a specific bit of development and then blow it away.) In this case, however, I saw some value in keeping this particular VM around for awhile. As such, I figured it deserved a license, which made sense since I know I get a Windows 11 Enterprise license via my Microsoft 365 E3 account. The question was how to make use of said license.
The Wrong Way
After my initial installation, I was logging into the VM with a local account; this came about due to the fact that my VM had no network connectivity until after the installation was complete. My first thought was to simply add another user to the machine that was my Office 365 account and log in using that. I tried going to:
Accounts > Other users
When trying to add a user this way, however, it only permits consumer Microsoft accounts to log in. Trying to log in with my Office 365 account would result in an error message that no Microsoft account matching the address existed. Next, I tried to link my O365 account by going to:
Settings > Email & accounts
This allowed me to add the account. It did briefly download some things and apply a bit of policy, but it certainly wasn’t a full-blown InTune deployment. Once the dust settled, I could easily access some of the data in that O365 account via the Windows 11 apps, but I was still sitting on an unlicensed Windows 11 Pro installation.
The Right Way
After that failure, I next stumbled across something that seemed more promising but was still slightly incorrect. I went to:
Accounts > Access work or school > Connect
After clicking Connected, I was presented with this screen:
Initially, I plugged in my email address, clicked Next and walked through the process. This essentially got me to the same spot as going through Settings > Email & accounts. The correct thing to do on the screen above is to ignore the email address field and click the link for: Join this device to Microsoft Entra ID.
After that, I logged into the account and the system went through a fairly involved process to enroll in InTune, apply a bunch of policies, and (mercifully) upgrade itself to using a Windows Enterprise license.