Windows 10’s Legacy? It’s Complicated (Premium)

Ten years ago today, Microsoft released Windows 10, kicking off a new era for Microsoft's core desktop computing platform.

As is so often the case, Windows 10 is being celebrated and mourned as we near the end of its 10-year lifecycle. But Windows 10 has a complicated legacy that's undermined by the enshittification that Microsoft built in to this product and then expanded over time.

So here's a different perspective on Windows 10.
8️⃣ The problems started before Windows 10
I was an early critic of the initially subtle ways in which Microsoft undermined the Windows experience. Windows 8 was widely and correctly criticized for forcing the entire Windows user base, all of which were using traditional laptop and desktop form factor PCs at the time, to use a "touch-first" and full-screen user interface with non-discoverable features. But Windows 8 also brought another unwanted first, advertising which was, at the time, limited only to the universal in-box apps that Microsoft bundled with the OS.

I described this as "a slippery slope" in an article I titled Microsoft Cheapens Windows 8 with Ads.

"When Microsoft announced that virtually every single PC user on earth would be able to upgrade to Windows 8 for just $40, I cheered the company," I wrote in November 2012. "But this low price is partially achieved by the bizarre addition of advertising in Windows 8, a move that I think cheapens the product ... apologists will explain that these ads aren’t in the OS user interface, which is true, and that you really have to hunt for them in the apps in which they do appear, which is also true. But this is a slippery slope, folks. If you accept a few banal ads in Windows 8 for $40, what would you accept in Windows 9 for $20? When does it stop? And why wouldn’t it get worse?"

I couldn't have been more right on this. The use of advertising--and advertising-like methods that include sponsored app placements, upsells, dark patterns, and more--escalated dramatically in Windows 10 and then again in Windows 11. By 2017, even those who disagreed with my earlier slippery slope designation were onboard. But by then, I had also found out how this had happened.
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Satya Nadella became CEO of Microsoft in early 2014, about six months before Microsoft announced Windows 10. At the time, he was largely unknown, and the first and only time I had met him in person, years earlier at a Visual Studio reviewer's workshop, I shook his hand, saying, "Oh, good, fresh meat." It's odd we're not pen pals now.

I later learned from friends at Microsoft that Nadella's first months leading the company were largely spent doing what new CEOs often do: Getting to know eat team within the company to figure out how it all works together. But Nadella was overtly aggressive about two key changes he would institute. The products each team made had to be profitable or have a path to profitability. And more problematic, those products had to align with the...