Crazy Eddie is Coming for Windows 11 (Premium)

In 1986, Steve Ballmer starred in a widely misunderstood internal video parody advertisement for Windows 1.0. But today, it seems prescient. What would it take to get you to upgrade to Windows 11? Or from Windows 11 Home to Windows 11 Pro?

How does $10 sound?

Let me quickly address the Steve Ballmer video first. If you Google this, you’ll find references to this video being a “1986 Windows Ad,” “Steve Ballmer promoting Windows 1.0 in 1986,” and so on. These are all incorrect. We forget this, but Microsoft used to record funny and corny videos internally to share with the company, and they were so popular that they would show them during Bill Gates keynotes at events. (One famous and memorable example: Bill Gates and Steve Ballmer spoofing the then-current VW “Da-da-da” ads.)

The Steve Ballmer video for Windows 1.0 is just a parody, an internal production that accomplishes exactly what it and so many future videos set out to do: Educate while being funny by spoofing something that was then well-known. In this case, it was spoofing the “Crazy Eddie” TV ads of that era. For example, this one. As for educational, once you’re done laughing at Ballmer’s over the top presentation, you’ll discover that Windows 1.0, a little-understood, poorly selling product, arrived with significant advantages over plain MS-DOS. And you got all that … wait for it … for the low, low price of $99.

Windows has changed a lot over the years, and anyone who’s been there for the duration will remember the highs and lows. The sudden surge in popularity with Windows 3.0 and 3.1. The explosive excitement of Windows 95. The partial switch to the NT codebase–and the loss of the NT brand–with Windows 2000. The blue and green experiences of Windows XP … and the resulting security nightmare that spawned Trustworthy Computing. The year’s long wait for Longhorn … and the resulting disappointment in Windows Vista. You know the drill.

Today, Microsoft is careening toward the end of support for Windows 10, the most popular version of the product Microsoft has ever made by usage. But as Laurent pointed out yesterday, Windows 10 still commands about 63 percent usage share just months ahead of that support expiration. This is unprecedented. Windows 7, the second-most popular Windows version by usage, had about 25 percent usage share by this point in the life cycle, and its replacement, Windows 10, already dominated, with 68 percent usage share.

There is so much to unpack here. And it is far too easy to look at this situation and invent a single cause. But I think the truth is far more nuanced, that there are many things that contributed to the situation in which Microsoft now finds itself. What I can say is that this isn’t because Windows 11 is somehow lacking in some way. Yes, that was true when the system first appeared in 2021. Indeed, its functional regressions are the stuff of legend. But not today.

Before you click that Comment box at the bottom of this post and start writing a heated retort about how Windows 11 still doesn’t let you put the Taskbar on whatever side of the display you prefer to use, please don’t. Anyone reading this is an outlier, a technical person with specific needs that don’t necessarily (if ever) represent the mainstream. We don’t get to see the hard data that Windows leaders of the past like Steven Sinofsky used to publicize to make a point, and I miss that. His explanation for killing Media Center was that telemetry showed that only a single digit percentage of Windows users ever ran the app, and of those that did, a high 90-something percentage were mis-launches that immediately closed it. You may still be nostalgic for that product, but the numbers speak for themselves.

There is nothing wrong with Windows 11 that is not also wrong with Windows 10. OK, that’s not entirely true: Microsoft more aggressively pushes enshittification in Windows 11 than it does in Windows 10, though all the elements are there in both. It’s just that Windows 11 is newer and the going concern. It’s getting more attention, and that’s both good and bad.

Put another way, Windows 11 includes many, many useful features that Windows 10 lacks. Its user interface is modern and still fresh, and it feels similar to the mobile OSes will all use more than PCs anyway. Windows 10, by contrast, is a user experience dinosaur with the vestigial remains of a UI that made sense on phones that haven’t existed for a decade but was always ill-suited for a desktop system. There is nothing nostalgic about Windows 10 beyond the much-needed shift back to focusing on desktop computing instead of touch/tablet computing. Another numbers-based reality: To this day, very few people use Windows as a tablet system. Again, please stay out of the comments. It’s OK if you’re that outlier, too. Just know you’re a tiny minority and that the iPad exists. Look into it.

Our little community is getting a little too set in its ways. I’ve pointed this out with the new Outlook, an app that generates far too much hate and far too little respect for how good it actually is and how far it’s come. Here, too, power users and the tech elite focus on nonsense legacy needs of the past instead of seeing the big picture. With Windows 11, what we got at first was a minor step forward from Windows 10 tied to an interesting attempt at simplifying a UX that was still far too complex for most people. These things are difficult work. You can’t simplify a product like Windows without losing things. I don’t always agree with what they lopped off. But I do respect the attempt.

More to the point, none of this–OK, most of this–is no longer true. Windows 11 has surged well past Windows 10 from a technical perspective thanks to the foundational changes in 24H2 and the security improvements tied to Copilot+ PCs and Windows Hello ESS. And Microsoft has–slowly, yes—improved the UX and smoothed the rough edges. Windows 11 isn’t just in a better place–a place those who have never created software of this magnitude would cynically argue is “what Microsoft should have shipped in the first place”–it’s literally better than Windows 10 across the board.

Again. You may have this specific picayune feature that “disproves” this claim. Whatever. It’s time to move forward.

So what would it take?

If you have aging hardware, there are workarounds–I document them in my book Windows 11 Field Guide, and you can regale us all with the tales of how well Windows works on your 4th generation Intel Core processor, I guess. But I will argue, not for the first time, that if you’re actually using a PC with a 7th generation or older Intel Core processor–or its AMD equivalent–that maybe it’s time for a new PC. No, not maybe. It is time for a new PC. So much has changed for the better since Intel burped out its 7th gen chips in 2016. Look into it.

Perhaps it’s the cost.

Window 11 is a free upgrade from Windows 10. But if you visit the Microsoft Store or any mainstream retailer, you will discover that Windows 11 Home costs about $140, while Windows 11 Pro will set you back about $200. So it’s more expensive than the Windows 1.0 that Mr. Ballmer was allegedly shilling in 1986. But as he asked, “How much do you think this advanced operating environment is worth?” $140? $200?

How about $10? How does $10 sound?

I was reading my news feeds this morning and I came across an article on a Mac-oriented blog promoting Windows 10 for $20. It noted that this was an easy and inexpensive way to acquire this system for use in a virtual machine in macOS. You can, for example, use Parallels Desktop to run Windows app side-by-side with macOS apps. (And yes, the thing you’re buying is a product key, not a box with software in it, and that key will work with the Windows 11 on Arm that’s required on modern Macs too.)

You’ve probably seen these promotions. You’ve probably wondered if they are legal or whether Microsoft will at some point swoop in and deactivate the software, leaving you in the lurch. I’ve wondered, too, though I never saw Microsoft ever doing anything to already-installed and configured Windows systems. I still don’t.

For years, I used a trove of stored Windows 7 and 8 product keys to activate Windows 10, mostly in VMs, but also on physical computers. They could also be used to upgrade Windows 10 Home to Pro. And then upgrade to Windows 11. I used to write articles about this. It seemed like it would never go away. And then, finally, it did. In late 2023, Microsoft stopped allowing us to use these keys to activate Windows 10 and 11.

At first, I was concerned. I’m not pirating software here, I have legitimate work-related reasons to activate test instances of Windows. But then I realized it didn’t matter. In most cases, I don’t need to activate (or upgrade) random PCs or VMs. But when I do, I can just avail myself of these cheaply purchased Windows 11 Home and Pro product keys. And so I have. Many times. It’s always worked out. I’ve had no issues at all, across multiple sellers.

But this Mac blog post caused me to take a look.

And sure enough, the online retailer they pointed me at is offering Windows 11 Pro for $20. Cheap. This same retailer is offering Windows 11 Home for $20 as well. But since it’s the same price, I would just get Pro.

The thumbnail and landing page for the Windows 11 Pro deal notes that the seller is a “Microsoft partner,” which is amusing. That seller is Smart Training Lab, and so I went to its website directly.

And I found an even better deal.

Smart Training Lab currently offers Windows 11 Home for only $10, as before. But it also offers Windows 11 Pro for just $15. Or … you can get two Windows 11 Pro keys for $20. That’s $10 apiece too. And that may just be the lowest price I’ve ever seen.

$10.

How much do you think this advanced operating environment is worth?

And it’s not just Windows. If you’re tired of all the nagging and the subscriptions, you can find standalone copies of various Office suite versions for next to nothing, too.

And I know what you’re thinking. But here’s what I’m thinking.

Who cares? If this were illegal, Microsoft would put a stop to it. And what’s the worst thing that happens? The software stops working? That won’t happen. But what if it does? You’re you. You’ve got this. You can recover from anything, and it’s not like you’re going to lose data. I’ve had too much success with these keys to worry about it. To be clear, I’ve not used the services noted above. But Google’s a thing. Look into it.

So go forth and be free. Spend a few bucks if and when necessary. Upgrade that Windows 11 Home-based PC to Windows 11 Pro. Or whatever. We can all be a little Crazy Eddie sometimes.