Something Happened ⭐

Microsoft has treated Windows as a second-class citizen since the Windows 8 debacle, and the problem has only escalated during Satya Nadella’s time as CEO. Since the launch of Windows 11, this product has been drowning in enshittification, and it seemed like things were going to keep getting worse because that’s what we came to expect.

And then something changed. Something … happened.

Microsoft has begun making happy noises about Windows 11, first in isolated cases and then, recently, in a more organized and regular fashion. Microsoft’s broader corporate ambitions and strategies had left Windows behind decades ago as the wider personal computing market shifted from computers to mobile, and as the software giant’s core competencies forced a transition into an infrastructure provider, first with cloud computing and then with artificial intelligence (AI).

Through it all, Windows kept delivering. As a legacy business driven largely by inertia, there wasn’t much growth to be had, even when Windows 10 exited support in late 2025. But thanks to its ties to the Fortune 500 and Microsoft’s biggest business customers, Windows has consistently dumped several billion dollars into the company’s coffers every single quarter. And yet Microsoft had ignored and even actively maligned the product and its users with enshittification throughout.

But there’s change in the air. Something happened. Is it real? Will be it persistent? And what drove this change?

? The seeds of our discontent

This is a tough time to be a Windows enthusiast and I assume there aren’t many left. To my mind, while the changes in the industry and to Microsoft specifically have had a negative impact on Windows, there was a silver lining, too. Today, most people do fun and casual activities on their phones and tablets, and that doesn’t just diminish the need for Windows, it also allows us to focus on productivity and work when we use a PC.

Interestingly, this aligns with the needs of the customer base. Two-thirds or more of all Windows users are business customers, not consumers. And those consumers who continue to use Windows typically stick to productivity and professional creator use cases because that’s when the PC’s larger display and keyboard, and the sophistication of desktop apps, are so advantageous. Yes, Windows relinquished its dominance of personal computing. But it’s also now a more optimal tool for productivity. I love that.

I would have loved it more if Microsoft had simply acknowledged this shift and then treated its customers with a bit of respect. But Microsoft relegated Windows to a backwater world led by B-teamers as the brightest minds at the company moved onto more lucrative career opportunities in Azure and AI. This was bad for Windows, but it was also bad for customers. And a knife in the back to any enthusiasts still holding out hope for a miracle.

I was not expecting a miracle, and I’ve tried to caution others to be realistic. As Cory Doctorow explains of enshittification, it’s not possible for a customer of any product or service to “vote with your wallet” because your vote doesn’t count or matter: Microsoft, in this case, is better served financially by ignoring or even hurting Windows and its users in its manic drive to secure its future in an AI world. You can and should make the right decisions for yourself, and do so selfishly. But you should also understand that Microsoft and other Big Tech companies will never care that you’re hurt or may leave the platform. We aren’t going to hurt Microsoft regardless of what we do.

There are two important asterisks to consider here, however. And these are things I have thought about, and a lot.

The first is antitrust. While Microsoft for several years evaded a lot of the antitrust attention that Apple, Google, and other Big Tech firms so richly deserve, it is now under the regulatory microscope again for its predatory practices in cloud computing, Microsoft 365 and Teams bundling, and more. And Microsoft just announced that Windows 11 has over one billion users, so that platform, too, can and will fall under scrutiny too.

Second, while you and I don’t matter to Microsoft, the Fortune 500 and Microsoft’s biggest business customers do matter. And these firms can vote with their wallets and materially impact Microsoft in a negative way. With the makers of other, simpler personal computing platforms racing to turn those systems into full-featured computers, the clock is ticking.

This may not be obvious to many individuals, but Microsoft has long given companies policies and other tools by which they can control the user experience their users see and protect corporate data, and these tools largely shield those companies from the enshittification we see as consumers. If you look over my Windows 11 enshittification checklist, literally none of my concerns apply to businesses.

But the B-teamers who ran Windows through the end of 2025 had their impact. And that impact was negative for everyone, including businesses. You may recall that Microsoft announced the Secure Future Initiative (SFI) in late 2023 to assure its business customers that it was serious (again) about security, only to admit two months later that it had been the victim of a state-sponsored hack of its corporate network. And then the CrowdStrike episode occurred, reminding the world that the security of the Windows kernel was being held ransom by security firms that refused to let Microsoft fully secure it.

And so we got a song and dance routine. Microsoft promised to work with the security industry, but those companies refused to relinquish their access to the Windows kernel unless Microsoft did so too. In the midst of its massive shift from cloud computing to AI, Microsoft announced that security, and not AI, was somehow its top priority. It then “re-affirmed” its commitment to security several months later, claiming progress. And in November 2024, it was back with something called the Windows Resiliency Initiative, which would bring SFI to this crucial but long ignored product.

There’s been some real progress, to be fair. The use of Rust throughout the Windows kernel and driver layers of the operating system. Individual features like Smart App Control and Quick Machine Recovery. But quality is a byproduct of good work. And B-teamers don’t do quality work. Just last month, the cumulative update (CU) that went out to all supported Windows 11 versions was so horribly broken that Microsoft had to issue two subsequent updates to fix the problems caused by the original CU. And that kind of problem does impact Microsoft’s most important business customers. This is exactly what no one wants to see. A lot of talk about quality while Microsoft is delivering everything but.

There’s more.

? This is all about AI

Microsoft’s insane AI push is also impacting its corporate customers. It has added AI features all throughout Windows and the Microsoft 365 apps and services, some useful and some broken or objectively pointless. It has pushed Copilot aggressively to a business customer base that could not care less about Copilot if they tried. Today, less than 3.5 percent of Microsoft’s corporate customer base that pays per-user per month for Microsoft 365 has opted to pay for Microsoft 365 Copilot as well. They’re all too busy signing up for Anthropic Claude, OpenAI ChatGPT, or even (God forbid) Google Gemini to care less about Copilot. Why? Because those solutions work and Copilot is inept.

I mentioned inertia. This is an important driving force for Microsoft’s business customers, perhaps the single most important one. And if Copilot were almost as good as any of that competition, it would be much easier—so much easier—for those businesses to simply adopt the Microsoft solution. But it says a lot about the lack of quality they see in Copilot that few have done so. These companies happily moved onto Teams, which was so successful that Microsoft was forced by EU regulators to de-bundle it from Microsoft 365. But Copilot? No thanks.

(Yes, Teams was essentially free, and Microsoft 365 Copilot is a paid product. But Microsoft has seen great success upselling customers to more expensive tiers of Microsoft 365. And its lack of success with Copilot speaks volumes.)

This is in many ways all about AI.

AI is a corporate imperative at Microsoft. It’s all Microsoft really cares about and this company has committed to spending over $140 billion this fiscal year just to build out an AI infrastructure that may never even be necessary. Business customers are ignoring Copilot, but they also have fears that AI will be used to siphon off corporate secrets or expose them to new kinds of security vulnerabilities. That’s reasonable. AI is notably insecure, after all.

The one thing that Microsoft can do to prevent an all-out revolt by these critical business customers is to assure them that it, and only it, can fully secure their corporate infrastructures. Not just from the usual threats, but from AI as well. And when you look at the changes we’ve seen recently, and view them through this light, it starts to make sense. Microsoft has pushed the enshittification in Windows 11 as far as it could, and now the only customers that matter are finally starting to push back. And so Microsoft is making changes.

Finally.

? What’s changing

Back in August 2025, Microsoft promoted Windows lead Pavan Davuluri to president of the company’s Windows + Devices division. In September, he reorganized this business to bring Windows client and Windows Server development together for the first time in several years. He now oversees both teams plus Core OS, Data Intelligence and Fundamentals, Security, and Engineering Systems.

This shift gave the three enthusiasts still holding a candle for Windows some hope. Davuluri probably means well, and I do like the guy, but like his predecessors, he also has to make Windows conform to Microsoft’s broader strategies. And as noted previously, that’s all about AI. And so he has been tasked with figuring out how to best integrate AI capabilities in Windows.

This is a bridge too far for many.

When he announced that he would be speaking about adding agentic AI features to Windows 11 at Ignite 2025, Davuluri was flooded with hate. This was unfortunate and unfair, and the functionality he and his team later announced was mostly innocuous and even reasonable. But the criticism didn’t stop. Customers don’t want AI slop, a term Satya Nadella and other Big Tech/Big AI executives have railed against. But they especially don’t want Microslop.

This is a potential extinction moment for Microsoft. Not for the company as a whole, it will likely always have a role to play in infrastructure, similar to IBM or other companies nobody gives a crap about. No, this is a potential extinction moment for Microsoft as a company that matters. Microsoft as a company that provides first-party products and services that customers—mostly business customers—actually want and will pay for.

And so things are changing.

Satya Nadella just announced two new top-level positions for engineering quality and security, both reporting directly to him. Interesting.

Microsoft just announced the Windows Baseline Security Mode and User Transparency and Consent, directly addressing all the concerns I noted above.

And there are smaller things, little pinpricks of life, like the reversal of two-and-a-half years of OneDrive enshittification in Windows 11 that Microsoft never announced or discussed but is slowly rolling out everywhere. And just today, Microsoft issued new Secure Boot certificates in partnership with PC makers to secure older PCs; all PCs manufactured this past year already include them.

These things combined with previous efforts to make Windows 11 suck less are starting to have an impact. We won’t fully understand that impact for months to come, but I hope that we will see similar quality pushes in the interim through Windows Insider builds that point to a way forward. A way forward that isn’t as dire and sad as that we’ve faced for the previous several years.

There are no promises and few firm commitments as yet. The future is still uncertain. But something happened. And now, things are finally changing for the better.

Rejoice.