Windows 10 Throwback: September 30, 2014 (Premium)

On Tuesday, September 30, 2014, I sat in a small audience with Mary Jo Foley as Microsoft’s Terry Myerson and Joe Belfiore, the former Windows phone “B-teamers,” explained their vision for Windows 10. I’ve been thinking about that announcement a lot lately and it’s interesting to look back on that day, and the intervening six and a half years, and ponder what happened.

The central promise of Windows 10, as I saw it that day, continues unchanged, at least at a high level. Microsoft had made the wrong bets on “touch-first” user interfaces and mobile apps with Windows 8, but Windows 10 was a decided shift back to traditional PC form factors, and desktop user interfaces and interactions.

No, Windows 10 didn’t completely shed the nonsense of the past. The WinRT mobile app model evolved into the Universal Windows Platform (UWP) and the temporary insanity of “One Windows,” where developers could theoretically create mobile apps that could run on PCs, tablets, phones, Xbox consoles, and specialty devices like Surface Hub. The Windows Store eventually morphed into the Microsoft Store, adding new content types only to then remove them over time. And Windows 10, of course, expanded on what I had previously described as the “slippery slope” of in-box advertising, and then made things even worse with bundled crapware and user activity tracking that could never be turned off completely.

Windows 10’s early years were marred by the “Creator Update” nonsense and aborted “bridges” strategy of 2016-2017 in which developers would be able to bring their app codebases from the web, Android, iPhone, and elsewhere to Windows. There were privacy-based challenges triggered by the incessant tracking, and Microsoft’s hand-waving responses, which I referred to as “privacy theater” because nothing it did addressed the central concerns: We still can’t turn off the tracking if we want to.

Then there was the embarrassment of Microsoft proactively admitting that it would miss its goal of one billion users in “2-3 years,” followed by the even bigger embarrassment of pushing that reality out through a partisan third-party blogger who tried to bury the news. And it turns out that Microsoft had been lying about the usage numbers for the first couple of years too. And speaking of lies, how many features did Microsoft promise to add to Windows 10 only to never do so? It’s kind of a blur.

But the biggest issue with Windows 10, hands down, is what Microsoft calls Windows as a Service (WaaS), a wacky and unsuccessful plan to issue two major new versions of Windows every single year and keep as much of the user base as possible on the most recent codebase. Businesses rejected this plan outright, forcing Microsoft to extend long-term support at least twice. And the resulting Windows version upgrades have been so unreliable and problematic---again and again and again---that Microsoft hasn’t even issued once s...

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