Most efficient way of licensing Windows?

I recognize that Microsoft licensing is never simple. It's been a while since I've had to revamp my parallels setup. I was looking to get more persistent Windows VMs for certain workloads. The development/evaluation licenses shutting down is annoying.

So, in 2023, what is the most efficient way to purchase/license Windows VM with Parallels as the Hypervisor? I can't really get a clear answer on this when researching Microsoft's site or on third party sites.

Should one acquire discounted retail license keys?

Or, can one leverage a Microsoft subscription (e.g., M365 E3/E5)? This E3/E5 licenses apparently have virtualization rights, but it's not clear how activation works with a host machine running MacOS. I like the idea of having some sort of pool of licenses I could draw from. Keeping track of license keys is not appealing.

How have you approached licensing Windows? What have you found to be simple and economical?

 

No one is licensing Windows?

 

I am using Windows on three Macs, one using Bootcamp, two using Parallels. In each case I have bought the second cheapest Windows Pro licensing key from Amazon. I never paid as much as $30, so a considerable discount. Each time activation has proceeded smoothly and the computer has been added to my Microsoft account. The keys have usually been sent through the post from an address in the UK, where I live, though once I had to obtain it by a secure log-in to a site in South America. If you go cheap, you don't worry so much about a key not working, but this has never been the case for me so far.

 

Thanks for the info, John.
Have you ever looked into some sort of subscription through Microsoft? Is it cost prohibitive?

 

I find a subscription directly with Microsoft for Office 365 reasonable value, as I use all five installations on the three Macs. I am not sure how a subscription for Windows would work, as activation attaches it to a particular device, and they would need a way to cancel activation if the subscription ended. I have read that Windows Pro may be moved to another computer, but have no particular experience of this, apart from re-installations, when I notice the Device ID changes. (In Bootcamp days, the machine serial number was recorded on the Microsoft Account.)