Hands-On with Windows 11 Enterprise: Are You Enshittified?

When I think about the enshittification of Windows 11, my mind immediately wanders to the various ways in which you might work around its worst behaviors. But there’s one potential option I’ve never tried, oddly. What would it be like if we could use Windows 11 Enterprise instead of Home or Pro? Would this solve any problems? Is this even possible?

Research ensued. OK, some Google searches. And some interesting finds.

If one were to, say, Google How to purchase Windows 11 Enterprise as an individual or similar, one might go down various rabbit holes. Tangentially, this query highlights one way in which AI might improve traditional Internet search because you’re looking for something very specific, not a list of weblinks, most of which go to pages about acquiring Windows 11 Home or Pro. But that is not the goal here.

In any event, you may be familiar with the notion of purchasing Windows 11 product keys online, not from Microsoft, but from a long list of shady-seeming online businesses that are somehow able to offer such a thing for $30 or less in many cases. (The retail price of Windows 11 Home is $125, while Pro is $200; you can get an OEM version of Windows 11 Home for about $100) I’ve availed myself of these, ahem, services several times in recent months because Microsoft disabled the ability to activate Windows 11 using a Windows 7 or 8.x retail product key; I have a ton of those from MSDN and/or TechNet, so I never had previously any issues activating different versions of Windows in virtual machines (VMs) and elsewhere.

What I hadn’t tried was buying a Windows 11 Enterprise key. Well, not inexplicably: I write for individuals, not businesses, here on the site, with the Windows 11 Field Guide, and elsewhere. And Windows 11 Enterprise isn’t directly offered to individuals. So I have stuck to Windows 10 Home and Pro. Logical enough.

But as everyone knows, Windows 11 came into our lives almost three years in imperfect form, with artificially restrictive hardware requirements, forced tracking, forced Edge usage and new default browser limitations, bundled crapware, and other issues. And Microsoft has aggressively expanded its enshittification Windows 11 since the initial release with forced Microsoft account (MSA) sign-ins, forced OneDrive folder backup, chaotic, frequent, and often untested feature updates, and other frustrations.

This bad behavior puts me in a bit of a bind. I’m technical enough to figure out workarounds when they exist, but I also have to experience and then document what’s really happening out there. I write about those workarounds for others as makes sense. But I also often can’t use them for myself in many cases. I’m the canary in this coal mine.

But the idea of using Windows 11 Enterprise has long been floating in the back of my brain, taunting me from time to time with the possibility of finding the answer. Something that might work for me in my day to day life on my own PC(s) and make real the claim I’ve often made: That I would happily pay to de-enshittify Windows 11.

I have long wondered why Microsoft doesn’t offer this out to its customers. And I have long imagined howthey might do so, either by making this a perk of a Microsoft 365 consumer subscription, similar to ad-free Outlook, or via a new or add-on subscription (similar to Copilot Pro or Copilot for Microsoft 365. The business model is proven and doesn’t require explanation.

But using Windows 11 Enterprise might be another option, assuming it’s inexpensive enough and actually solves the problems. (While moving to the European Economic Area isn’t a solution for me or most others, somehow subverting Windows 11 Home or Pro to implement their DMA compliance elsewhere is, of course, a potential option. Obviously, I’m looking into that as well.)