Microsoft at the Crossroads: Navigating the AI Backlash as Windows Celebrates 40 Years

It feels like Microsoft is blindly racing toward another Windows 8 situation. Windows 8 was arguably the most divisive release of Windows in its 40-year history, as Microsoft attempted to overhaul the operating system for a touch-first future. Spooked by the iPad, the company shipped a radical overhaul that ditched the familiar Start menu and left users frustrated and confused. They weren’t quite ready for the future that Microsoft envisioned.

As I look at Windows 11 today, on the 40th anniversary of the operating system’s release, its ongoing AI overhaul is starting to feel similar to that controversial redesign.

Microsoft detailed its vision for Windows to become an “agentic OS” at its Ignite conference this week. The software maker is building AI capabilities directly into Windows to allow agents to control your PC for you, all while it continues to infuse AI features and Copilot buttons into all corners of the OS.

For some Windows users, it’s already all too much.

Windows chief Pavan Davuluri announced the agentic OS plans in a post on X last week, and there was an immediate backlash in the hundreds of replies. “It’s evolving into a product that’s driving people to Mac and Linux,” said one person. “Stop this nonsense,” said another, and one reply even asked for a return to the Windows 7 days of a “clean UI, clean icon, a unified control panel, no bloat apps, no ads, just a pure performant OS.”

There could have been hundreds of more comments, but replies to Davuluri’s post were locked a couple of days later. He did eventually respond to a post from well-known software engineer Gergely Orosz, who criticized Windows’ “weird direction” and questioned Microsoft’s commitment to developers. “We care deeply about developers,” Davuluri said in response. “We know we have work to do on the experience, both on the everyday usability, from inconsistent dialogs to power user experiences. When we meet as a team, we discuss these pain points and others in detail, because we want developers to choose Windows.”

The problem for Microsoft is that care and attention to detail feels lacking in Windows these days. Microsoft has a challenge of building an operating system to fit the needs of more than a billion users, and it seems to be pissing off a lot of them right now by focusing on AI instead of improving the fundamentals.

Whenever I write about AI features in Windows, it’s near-impossible to find comments praising the new additions. I’ve tried Copilot Voice and Vision multiple times and most of the time I end up with results like my colleague Antonio found this week. Copilot seems amazing when its magic trick works, but when it fails time and time again, you rapidly lose trust in it.

During my recent break I asked Copilot Vision to help me use a UV bottle sterilizer I had purchased recently. I didn’t have the manual nearby, and the sterilizer has a confusing number of buttons. Copilot Vision recognized it was a sterilizer, but missed the key part that it was a UV model, so it asked me to fill it with water. If I had done that and turned it on, I would have ended up with a kitchen full of smoke and a broken device.

You could forgive this poor advice if this was a beta feature that was hidden away in Windows and years away from widely shipping, but it’s not. Instead, Microsoft is using it as a key marketing tool for its operating system, employing TV ads to encourage people to talk to their PCs. It’s even paying influencers to promote Copilot, and it had to quietly delete an influencer video where the AI assistant embarrassingly incorrectly identified Windows settings.

Microsoft’s push to get people to talk to a PC or let a computer control itself also takes away from why Windows has existed for 40 years. App developers use it to build new platforms, surgeons and doctors rely on it in hospitals, and even ATMs use it to distribute cash around the world. You only need to look at the chaos from the CrowdStrike incident last year to see how much critical infrastructure uses Windows.

It’s this reliable tool that Microsoft seems to want to reshape into something autonomous, increasingly built for AI agents instead of humans. In a recent Dwarkesh Podcast interview, Microsoft CEO Satya Nadella admitted that the company’s entire business is moving in this direction. “Our business, which today is an end user tools business, will become, essentially an infrastructure business in support of agents doing work,” Nadella said.

He likened this to how servers became virtualized, creating even more server availability for cloud infrastructure. Now there’s an increased demand for cloud versions of Windows 365, so that agents can use a computer to get human work done. “We’re going to have an end user computing infrastructure business that I think will keep growing,” Nadella said. “Because guess what? It’s going to grow faster than the number of users.”

While Nadella is looking way ahead to a future where this stuff actually works, if indeed it ever does, Davuluri is left trying to shape Windows into a pizza with a billion toppings that please everyone, with a side of AI.

”We are on a journey of evolving what Windows is like for the future,” Davuluri said in an interview with The Verge earlier this month.