Let’s Talk About Windows Updating. Again. (Premium)

Microsoft’s strategy for updating Windows has been a moving target since the release of Windows 11 version 22H2, and it’s hard not to believe that the software giant has been making it up as it went along.

To be fair, this has been true for a long time. After the release of Windows 8, Microsoft kicked Steven Sinofsky out and immediately began dismantling his most onerous mistakes. Everyone probably remembers the shift to Windows 8.1.x and then Windows 10, which rolled back the tablet- and touch-first silliness and returned the focus to the desktop and traditional interaction techniques where it belonged. But I suspect few remember another shift, though its repercussions were just as big: starting with Windows 8.1, Microsoft transitioned Windows updating from the plodding pace that Sinofsky favored to a new “rapid release” model that persists to this day.

The company, he said, was moving to a “rapid release cycle. Rapid release. Rapid release,” Microsoft CEO Steve Ballmer said at the time, as I described most recently in Programming Windows: Aftermath (Premium) and in the book Windows Everywhere. “Rapid release cadence is absolutely fundamental to what we’re doing. You will see a heck of a lot of movement, a heck of a lot of innovation, a heck of a lot of responsiveness, all coming to market in a very, very rapid timeframe.”

The “rapid release” strategy of Windows 8.1.x evolved into “Windows as a Service (WaaS)” with Windows 10 and now “continuous innovation” with Windows 11. From a high level, these name changes read as new leadership using new terminology to put their own stamp on what might appear to be the same strategy under the covers. I’m sure that played some role, but the ways in which Windows could be---and has been---updated over the years, some important truths stand out. Microsoft has dramatically expanded the ways in which it can update Windows. It has dramatically expanded the reliability of these updates, though problems do crop up from time to time, of course. And it has clearly been making it up as it went along.

To date, nothing spoke to that last point more clearly than former Windows chief Terry Myerson’s claim that Windows 10 would be “supported for the lifecycle of the device,” a nonsensical statement that didn’t make sense 8 years ago and makes even less sense today given what’s happened in the interim. But the advent of Windows 11 and “continuous innovation” provides even more dramatic proof of that point. Windows 11 changed things yet again, sure, but the updating strategy has already shifted several times since Microsoft announced this OS two years ago. Keeping up with the changes, delivered as they were without (almost) any warning or discussion on Microsoft’s part, has been one of the most challenging times of my career. I haven’t had to decipher the meaning of what the Windows group was doing like this since the dark days of Windows 8 and Sinofsky’...