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.)

So back to that theoretical discussion about acquiring a Windows 11 Enterprise license. Were one to Google such a thing, they would eventually find a service that offers such a thing. And probably for much less than they’d expect. Suspiciously less, even. This isn’t something I can recommend per se. But in the interests of uncovering the truth, I took this leap of faith, acquired a key, and hoped for the best. While fearing the obvious.

You might optionally install Microsoft’s free evaluation version of Windows 11 Enterprise, of course. But I wanted to make sure I could activate this software: I can’t think of anything worse than learning that Enterprise is perfect but I can’t even use it.

I could have probably used the evaluation download to install Windows 11 Enterprise. But I made it myself by customizing Microsoft’s Media Creation Tool (MCT), which you download from the Microsoft website. The installation media you create with MCT doesn’t usually offer Enterprise as an option, but you can run the MCT installer from the command line using the following option switches and it will create installation media for Windows 11 Enterprise specifically. (This assumes you’re in the same folder as the MCT installer.)

.\MediaCreationToolW11.exe /Eula Accept /Retail /MediaArch x64 /MediaLangCode en-US /MediaEdition Enterprise

This has a nice side effect in that it pares down the MCT installation wizard nicely, but it also introduces an issue: MCT prompts you to input a product key before it will create the installation media. I didn’t want to use the product key I’d just purchased, but it turns out you can bypass this by entering what’s known as a generic Key Management Services (KMS) key for this purpose: This key will let you install Windows 11 Enterprise but not activate it. The generic KMS key for Windows 11 Enterprise is NW6C2-QMPVW-D7KKK-3GKT6-VCFB2.

Once I had the Windows 11 Enterprise installation media, I rebooted the business-class PC I had selected for this test and used it to run Windows 11 Setup.

As most readers know, this process is divided into two parts, the old-school first-boot experience (as I call it, I’m not aware of a formal name for this), and the more graphical Out-of-Box Experience (OOBE), the part all Windows 11 users see (this is what appears when you first power-up a new PC). Windows 11 Enterprise works similarly, but the first-boot experience is subtly different, while the OOBE is more dramatically so.

The first-boot experience was quite familiar: The only notable change was that the traditional, long, and unreadable end-user license agreement (EULA) was missing in action and replaced by what amounts to a terse warning.

Then the OOBE appeared and started off normally enough, displaying its initial “Is this the right country or region?”, “Is this the right keyboard layout or input method?”, “Want to add a second keyboard layout?”, and “Let’s connect you to a network” screens.

After that, everything was different.

The OOBE skipped the “Please review the License Agreement” and “Let’s name your device” screens entirely. And then, instead of the “How would you like to set up this device?” screen that lets you choose between an MSA and Microsoft work or school account sign-in, it displayed a “Let’s set things up for your work or school” screen. That, yes, forces you to sign in with to a work or school account, Microsoft’s not-great name for its Entra ID-based commercial sign-in accounts.

I happen to have one of these, as I maintain a Microsoft 365 commercial account with a custom domain for testing purposes. But this will be a blocker for most people, and a workaround is needed. I will research that, but for this first install, I took the path of least resistance and signed in with my Microsoft 365 commercial account.

The OOBE then quickly flashed that black “Hi” screen we typically see at the end of this process, went dark, and then came back up to a configuration screen for Windows Hello, which noted that my organization requires me to use this functionality.

I skipped the facial recognition offer as always and was then presented with the familiar “Set up a PIN” screen, which makes sense on two levels: Windows 11 requires a PIN when you sign in with any account that has a password, plus my organization of one apparently requires this, as noted above: A PIN is the most basic form of Hello. Then I discovered that my organization also requires a 6-digit PIN, something I will try to fix later in the Microsoft 365 Admin portal.

After that, I made my usual configuration changes in the “Choose privacy settings for your device.” But that was it for the OOBE: It skipped the “Let’s customize your experience” screen, and the advertisement and dark pattern screens for Phone Link, Microsoft 365, Xbox Game Pass, OneDrive folder backup, and recent browsing data (which is really about letting Edge siphon your Chrome data every time you launch it)

I was then dumped immediately into my new Windows 11 Enterprise Desktop. Which is curiously identical to what we see in Windows 11 Home and Pro, with Widgets, Search, and Copilot all enabled, and the standard set of Taskbar shortcuts.

The Start menu, however, was the same spartan affair you get with Tiny11 and the super-clean install method I document in the Overcome Windows Setup Annoyances chapter in the Windows 11 Field Guide.

Before exploring further, I did the usual maintenance tasks. I spent about 30 minutes bringing this PC up-to-date via Windows Update (over two reboots, and I enabled the “Get the latest updates as soon as they’re available switch”). And then I updated all the in-box apps with the Microsoft Store app.

While that was happening, I ran Microsoft Edge for the first time and noted that it prompted me to import my data from Chrome (which I always decline) but did not display the privacy-stealing “Let’s make the web work for you” screen I caution readers about.

This triggered a quick check of Edge settings as documented in the Set Up Microsoft Edge Correctly chapter in the Windows 11 Field Guide to make sure it wasn’t autoconfigured to follow me around the Internet. Here, I was delighted to see that not only was this feature not enabled by default, it was disabled entirely and can’t be changed. Love it.

With Edge up and running, I downloaded and installed HP Support Assistant to make sure this PC—I’m using the older ZBook Firefly laptop I brought home from Mexico City recently—had all the latest drivers. It provided 8 drivers for me to download and install and then prompted me to reboot the PC. Which I did.

With all that done, it was time to take stock and make a few observations.

With all the updates installed, Windows 11 sat at build 22631.3374, so it was completely up-to-date.

Widgets was over there doing its thing, displaying notification bangs and animations, so I had to configure that feature as always. In my case, that means disabling notifications, the “Open Widgets board on hover” feature, and “My feed.”

Start remained minimal, with just the three icons—Edge, Settings, and File Explorer—in Pinned. I was curious if it would start populating with more shortcuts after I updated the apps, but no.

Search didn’t display the distracting consumer Search highlights interface, which, I believe, is tied to signing in with a work or school account: The “Show search highlights” settings in Search permissions is enabled, but you get a more spartan display that integrates with your organization’s documents and other data. (Toggling that option changes nothing.)

The Copilot button was inexplicably still positioned at its old default location to the right of the Search bar. OneDrive didn’t automatically sign in, so I did so, using my work or school account, and was prompted to enable folder backup (which I declined). And Do not disturb was enabled, as is the case with new Windows 11 Home and Pro installs.

Launching File Explorer, I could see that it used the same default configuration we get in Home and Pro, and then some: In addition to the Favorites and Recents section in Home, there’s a Recommended section that only Microsoft 365 commercial customers see. Plus another unique and related option in Folder Options, “Include account-based insights, recent, favorite, and recommended files” option. I left all that alone for now but disabled “Show frequently used folders” because I don’t like random folders showing up in Quick access.

Scrolling through Start’s All apps list, I uninstalled Cortana, Mail (and Calendar with it), Maps, and News, surprised that they were even there in the first place. Then I configured fingerprint sign-in, so I can skip typing the longer PIN. And then I renamed the PC—to Enterprise after briefly flirting with USS-Enterprise—and rebooted as prompted.

It was go time.

By which I mean, it was time to activate Windows. Or at least try: As you might imagine, I was suspicious of that key I had purchased.

There are several ways to kick off Windows 11 activation, but Setup is nice enough to prompt you to do so when you launch the app. So I found the product key in my email, copied it to the Clipboard, and then clicked “Activate now” in Settings. The resulting screen, with its scary red text, was initially off-putting.

But then I quickly realized that this was because I had used a temporary key when I first set up the installation media. So I clicked “Change” next to “Change product key,” pasted the key I had purchased into the “Enter a product key” window that appeared, clicked “Next,” clicked “Activate,” and … held my breath.

It activated immediately.

Interesting. Very interesting.

From there, I would normally personalize the PC a bit and then install the apps I want using my custom winget install script. Indeed, I started down that path by first configuring the Microsoft Store to use my Microsoft account (MSA), but then thought better of it. I may still test that configuration, but what I wanted to experience first was using an MSA sign-in with Windows 11 Enterprise.

To do that, I added my MSA as a sign-in using the Settings app (Accounts > Other Users > Add other user > Add account) and gave it administrator privileges.

Then I signed out, signed in with the MSA, and stepped through a suddenly familiar OOBE in which I declined Windows Hello facial recognition, configured a PIN (which, yes, must be 6 characters long because the initial work or school account sign-in configured policy from my organization to the PC), and then went through the same steps as before, with one exception: After that initial black “Hi” screen appeared briefly, the OOBE displayed the “Back up your files with OneDrive” screen, giving me the option to choose “Only save files to this PC,” which I selected. Then I configured the options in the “Choose privacy settings for your device” as always.

And then I was dumped right into the same Desktop I saw with my work or school account, with the same spartan Start menu. And the same misplaced Copilot icon. There were no Windows Updates to install, of course, but I updated the in-box apps using the Microsoft Store, uninstalled the same handful of apps noted above, and made a few small configuration changes to the theme, Widgets, and File Explorer (which didn’t display the Recommendations section with my MSA, of course).

Then, while waiting for OneDrive to finish syncing, an interminably long process, and poised for it to screw me over my silently enabling the folder backup feature I previously declined, I used my winget app install script to install all my apps, as is normal.

That took a while.

But when it was done, OneDrive was all synced up. And when I checked on folder backup—a PTSD-based behavior due to how often it auto-enables itself—I was greeted by a reminder that you can’t even configure OneDrive folder backup on a PC that is also configured with OneDrive for Business.

I knew that was the case when configuring OneDrive (consumer) and OneDrive for Business in the same Windows sign-in. But I didn’t realize it applied to other sign-ins on the same PC. Interesting. And, in my case, ideal: My goal is for it to never silently enable this feature and now it can’t. (Note that this doesn’t require Enterprise: This happens with Windows 11 Pro as well.)

There is a lot more to do here, and as was the case with Tiny11 before, I’ll keep using this PC over the next several days to see what changes. I’m expecting the Copilot icon to skip on over to the right side of the Taskbar, where it belongs, for example. But I will eventually experiment with other configurations too. Removing the Microsoft work or school sign-in account to see what, if anything, changes. And maybe trying to figure out a workaround to the initial work or school sign-in account requirement: There’s a good chance that the workaround I document in Overcome Windows Setup Annoyances that lets you sign-in with a local account might work, for example.

More soon.