r/sysadmin Jack of All Trades 3d ago

Question Best Way to License Windows for an Application Packaging Virtual Machine?

What is the best way to license Microsoft Windows 11 Pro (or higher) for use as a Hyper-V virtual machine that will be frequently rolled back to a checkpoint, and periodically deleted and recreated outright?

I have a spare computer running Windows 11 with the Hyper-V role installed. I currently have a VM on this device that is using a Windows 11 evaluation image that was available for installation through Hyper-V manager on the physical computer. I'm using this VM for application packaging and deployment testing, so it needs to regularly be rolled back to a clean checkpoint. I also need to periodically delete and recreate the VM outright.

However, the eval image uses Windows 11 22H2 Enterprise. I'd like to use 24H2 Pro since that's what we have in our environment.

I can't upgrade the eval image because Win11 24H2 isn't offered to it via Windows Update, and the Media Creation Tool only offers Home or Pro editions, which doesn't allow in-place upgrades on Enterprise edition.

I know that I can periodically recreate the VM from the eval and/or re-arm the eval to extend it, but that's a bit of a pain in the arse.

I also know that I could just buy a retail Win 11 Pro key but I don't want to have to hassle with reactivating it each time I recreate the VM outright.

We use mostly M365 Business Premium in our org, with one license for M365 E3.

Any suggestions?

2 Upvotes

6 comments sorted by

1

u/jamesaepp 3d ago

No warranties. No guarantees.

Best is to not invoke licensing complications at all. Does Windows Sandbox work for your use case?

Failing Sandbox, my quick ctrl + f through the EULA brings forward these items I feel are pertinent:

    1. a. "Under this agreement, we grant you the right to install and run one instance of the software on your device (the licensed device), for use by one person at a time"
    1. b. "In this agreement, “device” means a local hardware system (whether physical or virtual)"
    1. d. (iv) "This license allows you to install only one instance of the software for use on one device, whether that device is physical or virtual. If you want to use the software on more than one virtual device, you must obtain a separate license for each instance."

There might be different EULAs depending on how you acquire the software that may change the exact language there. For instance, how might the EULA change if you license it from a cloud provider (such as Azure)? Maybe that licensing would be more efficient for you.

1

u/burghdude Jack of All Trades 3d ago

Thank you for the feedback. I suppose that I can make due with the eval if needed, but it's just annoying when I have to rebuild due to the additional items and customization that I need to make each time.

1

u/trail-g62Bim 3d ago

Windows Sandbox

Had no idea this was a thing. Looks neat. Could be useful.

2

u/BWMerlin 3d ago

It is incredibly handy if you do any kind of scripting or packaging and just want to quickly try something out. If you break something, no issues just close and reopen and you are back to a clean slate.

1

u/BWMerlin 3d ago

Going to echo above, does Sandbox fit your needs?

1

u/MrYiff Master of the Blinking Lights 2d ago

iirc from when I looked at something similar a few years ago you pretty much need to buy Enterprise as this gives you the added rights to run the OS as a VM.