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’s word-filled yet content-free mammoth blog posts.

There have been two moments (pardon the pun, insiders) of light, however, even in this darkest and most confusing of years.

The first came back in March, a dizzying time in which I was struggling to understand the steady stream of updates coming to Windows 11, Microsoft quietly issued a post to a blog few know about—as opposed to blogs.windows.com where it belonged—explaining that it was now issuing preview versions of its monthly feature updates for Windows 11 on the Tuesday of a given month’s Week D (fourth week). This stunning bit of clarity, delivered in semi-secret, was nonetheless an important bit of understanding, another piece of the puzzle in place.

The second came, just as quietly, this past week. On Thursday, Microsoft revealed, again via that same semi-hidden blog—and not blogs.windows.com where it belonged—that Windows 11 version 23H2 will be delivered as an enablement package and not as a full Feature Update, which would require a much lengthier and complex rollout schedule. There is a big discussion to be had around that decision—Microsoft has used this streamlined version upgrade approach on several Windows 10 versions, but it basically signifies that this is not a big update—but just as importantly, Microsoft quietly issued a whitepaper describing its strategy for updating Windows.

Why is this important? Because it’s the first time Microsoft has ever formally described its strategy in any detail since the silly “for the lifetime of the device” days of Windows 10. So here we are, 8 years into Windows 10 and (almost) 2 years in Windows 11, and Microsoft is finally describing how it’s updating these two Windows versions. Tellingly, this document is identified as “Version 1.0, July 2023.” It’s almost like Microsoft didn’t even have such a document, and thus a written-in-stone formal strategy, internally before now. (I actually believe it did not.)

This document is also important because it suggests that we’ve reached the end of the constant changes to Windows updating that we’ve experienced since September 2022, when Windows 11 version 22H2 first arrived. I don’t literally mean that Microsoft won’t change things again, and I could even see the next year being just as confusing as the last. But now that this document exists, Microsoft’s customers will reasonably expect updated versions of this document when and if things change. That is, future changes, regardless of the cadence, will hopefully be documented publicly so that I, and people like me, no longer have to speculate every month as has been the case recently.

Or, maybe the cynical view will win out. This is Microsoft, after all. And I can see a future in which the release of this document, and the transparency it brings, stands as a one-off moment of time, never to be repeated again.

We’ll see. But in the meantime, I recommend that anyone interested in this topic take the time to read the whitepaper, which pertains to both Windows 10 and 11 and is reasonably complete when it comes to explaining some of Microsoft’s often-contorted language use. I always seek clarity in my writing, and so Microsoft’s insistence on clarity-adjacent (or averse) language is both frustrating and amusing, with terms like shared servicing model, enablement packages (eKBs), and shared branch appearing in just the first few dozen words. Microsoft also needlessly obfuscates, as when it uses the term “feature update” to mean several different things, all the way from individual feature releases to big-bang version upgrades. It’s no wonder I’m on a hair trigger all the time.

The changes that occurred during the WaaS (Windows 10) era and now with “continuous innovation” (Windows 11) are perhaps most confusing to those of us who cut our teeth on the traditional updating models of the past, where Microsoft would issue a new Windows version roughly every three years, support each for 10 years, and issue service packs (and, briefly, feature packs) to each during their support lifecycles. Beta testing a new Windows version during this era wasn’t in any way confusing: you were testing some version of Windows, not some collection of features that may or may not be released with or unrelated to some version of Windows. Release milestones were obvious.

Since then, the world has changed, and with the rise of the web and then mobile, Microsoft has tried—unsuccessfully at first but, admit it, more successfully recently—to adapt Windows to the ways in which these platforms are updated. For example, web apps and platforms can be updated at literally any time, and it only needs to happen once since users can simply hit refresh in their browser to get an update, no matter how big. And modern mobile platforms—starting with the iPhone—initially adopted an annual version upgrade cadence that has since evolved into include a “continuous innovation”-like the rollout of new features throughout the year. Windows, despite its legacy codebase, is basically keeping pace with the new(er) kids on the block.

I must be honest here. I still find Microsoft’s new approach confusing, and I’m not sure if this is just me being middle-aged or if it’s just that this strategy is actually complex. But when I read paragraphs like the following, I can feel my mind shutting down.

“Instead of forking the Windows 10 version 1903 branch to create a new one for 1909, we used the same branch and simply added the new or enhanced features to the 1903 branch. When the new code was ready, we included it in the monthly updates (LCUs). Those were released as the monthly updates for Windows 10 version 1903. That new code, however, was disabled. Those new features were not active, and version 1903 remained the same. Think of it as having the new feature code for what would become Windows 10 version 1909 being slowly staged on the 1903 devices.”

What Microsoft is describing here is the point in time in which beta testers—people who enrolled in the Windows Insider Program to test a specific Windows version—stopped doing what they were originally doing. And it was the point in time in which this new way of adding features started filtering out to the world at large, or what I think of as “stable.” With Windows 10 versions 1903 and 1909, this was not a big deal, as version 1909 was not a major upgrade. But Microsoft would take this success in which it could successfully deliver small updates annually and now do so monthly. And sometimes, more often than monthly.

It did so quietly and without much discussion. With Windows 11, Microsoft thrilled its business customers by claiming that it would only deliver one Feature Update (version upgrade) annually (down from two annually with Windows 10), but it glossed over the fact that it would, in fact, deliver new features throughout the year. The net effect is that Windows 11 users get a lot of new features each year, but they’re delivered continuously instead of mostly in one big-bang feature update.

This shift, which started with the latter versions of Windows 10, necessitated that confusing (to me) related shift in the Windows Insider Program in which each channel no longer lined up with a specific Windows version. That Microsoft also expanded the number of channels in the Insider Program is likewise confusing (again, to me). But whatever your opinion on this matter, the Insider Program in no way resembles the original. And perhaps because of lackluster feedback and disinterest, Microsoft has started testing new features with the public, a practice I find objectionable. Mainstream users did not sign up for that.

Anyway, there’s an interesting amount of transparency in that whitepaper. It discusses the recent major Windows code branches, the resulting Windows versions, and the frequency and schedule for interim updates that will be shipped to each. And it’s quite explicit: we will be getting monthly feature updates, and these updates negate the need for even annual version upgrades. Windows 11 version 23H2 speaks to this. Yes, there will be future versions of Windows 11 (24H2 and so on) that might be delivered via a more traditional model that updates to a new code branch and triggers new hardware and software compatibility issues. But not always.

In the past, this happened semi-secretively, and, honestly, not many customers need to even know about this. But it’s always nice when a Windows upgrade (never described as such, of course) happens quickly and with little disruption. This new disclosure, aimed at business decision-makers and system administrators, can also benefit us, the enthusiasts who want to know more about how the sausage is made and, perhaps more important, want or need to understand the system they’re using and what it’s doing. And to be clear, when it comes to servicing, it’s doing a lot these days.

I criticize Microsoft for its lack of transparency, its inability to communicate effectively, and for barely or not testing new features before releasing them to the public. That all stands, and Microsoft needs to do a better job at each. But this new whitepaper is a fascinating and appreciated bit of documentation that answers questions. I hope it’s the start of a new era of transparency, but if this is all we get for a while, that’s not unexpected. I’m still happy to have it.