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.

?‍? Advertising

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 direction he championed at Microsoft. That is, they had to make sense as cloud-based and/or subscription-based offerings.

Some product groups, like Office, made this transition fairly seamlessly. Some, like Xbox, pushed a future in which the platform could be made to transition in time. But some, like Windows, presented unique challenges. In the enterprise, Windows had long been a subscription offering thanks to Software Assurance and Microsoft’s other volume licensing programs. But consumers weren’t interested in paying for OS upgrades, in part because of infamous reliability issues, and in part because Apple had, by then, starting giving away Mac OS X upgrades to existing users. And they certainly weren’t going to pay for a subscription.

Terry Myerson was given a terrible task by Nadella, but with a potentially lucrative reward. Microsoft would make Windows 10 free for those on Windows 7 and 8.1 on PCs and Windows Phone 8.1 on phones, and it would make future upgrades free as well. But in return, he would guarantee at least one billion installs of the OS to put it on par with Android and iOS, and he would monetize the consumer side of that user base through in-box advertising, sponsored crapware app placements, upsells to OneDrive storage and Microsoft 365 subscriptions, and more.

As controversially, Windows 10 would do away with the traditional 10-year support lifecycle–which is ironic, given that it would go on to have a 10-year support lifecycle, regardless–and would vaguely support the system “for the lifetime of the device,” a measure that was never defined. Microsoft would deliver two major version upgrades each year, though each would still be called Windows 10. Those upgrades would entice users with new features in an ultimately vain attempt at capturing the engagement Microsoft saw, but did not enjoy, on mobile. And they would be easy to install, and reliable. Somehow.

That last bit was particularly enticing to Satya Nadella, with his head in the clouds. Though Windows 10 was a legacy, on-premise client platform containing some of the oldest vestigial software code in the company, it would be updated seamlessly, and regularly, just like a cloud service.

And that scheme was called …

?‍? Windows as a Service (WaaS)

Terry Myerson revealed Windows as a Service (WaaS) at the January 2015 consumer event for Windows 10, six months before the product’s release to the public. That’s when Microsoft announced that Windows 10 would be a free upgrade, and it’s when it also announced Surface Hub and HoloLens. And so this part of the event is perhaps one of the least well-remembered. But I remember it clearly.

“When you first heard the term ‘Windows as a service,’ you probably thought ‘subscription service,’ and many assumed that Microsoft would of course eventually be coming to users with a collection plate, asking to be paid,” I wrote at the time. “This is not the case. This automatic updating requirement is simply ‘Windows as a service’ implemented in running code.”

“Once a device [PC] is upgraded to Windows 10,” Terry Myerson said at that event, “we will be keeping it current for the supported lifetime of the device, keeping it secure, introducing new features and functionality to our customers over time. We think of Windows as a service.”

At that, I leaned into Mary Jo Foley and asked whether she had heard that like I had. It wasn’t said explicitly, but it sounded to me like Microsoft was going to require that Windows 10 upgraders let their PCs be updated. She agreed, and after the event, as we were ushered between buildings on the Microsoft campus as we headed toward the meeting room in which we would be recording Windows Weekly, we asked about this. And we were told that, yes, Microsoft would require anyone who received the free Windows 10 upgrade to keep the system up to date. We would learn more about this later, we were told.

As it turns out, this wasn’t tied to the free upgrade. Any individual using Windows 10 would be forced to install updates as they appeared in Windows 10, though there were limited ways to push some back temporarily.

Windows as a Service was “great for consumers, great for developers, and great for the security of enterprise customers,” Myerson claimed, though the latter would fight this change and win some concessions early on.

On some level, keeping the Windows 10 user base up-to-date is a good idea, especially for security reasons. But Windows as a Service had issues, too. It took Microsoft several years to make this process reliable enough that it could be trusted. It upgraded–not updated–the OS twice per year, forcing major Windows versions onto everyone’s PCs. And it delivered tons of new features, most of which were later taken out of Windows because no one wanted them in the first place.

“Windows as a Service is not just unsustainable, it’s impossible,” I wrote in 2017. “The idea is that we’re all on the newest version of Windows, and because everyone is up-to-date, we’re all safe, and Microsoft can more easily and quickly respond to new security threats. But this system is actually dramatically more complex than the old scheme by which Microsoft simply supported all Windows versions for ten years. And it is riddled with PC configuration-specific and enterprise exceptions that make the entire thing an impossible mess.”

Amazingly, Microsoft eventually figured it out. After several years of screwing up users’ PCs and creating new instabilities everywhere, Microsoft finally honed WaaS in ways that made it much more reliable, in part through telemetry that would ensure that updates went out to known-good configurations first. But that was its own can of worms: In making WaaS work, it was able to evolve this into what it now calls “continuous innovation” in Windows 11, and new features and other updates starting arriving even more rapidly, leading to the chaos we see today.

But that is, of course, another story.

? One billion

With Windows 10, Microsoft didn’t just have to overcome the problems it had created for itself with Windows 8, it had to overcome an even bigger problem. With the rise of the iPhone and then Android and the iPad, mobile had become the primary personal computing platform of choice, and the PC was in decline. Windows 8 had tried and failed to address that problem. So the new Windows team would need to think differently.

Instead of discrete x86 and Arm PC platforms, Windows 10 would expand to become a single platform across multiple device types and form factors, all served by a single app platform for developers and a single app store for users. This platform, eventually called One Windows, would see Windows 10 come to phones, small tablets, Tablet PCs, laptops, desktop PCs, Surface Hub (meeting room smart screens), HoloLens (augmented reality), and the Xbox (video games).

This diversity would help Microsoft get Windows 10 out in the world on one billion devices “within two to three years,” Terry Myerson claimed. But by the time Windows 10 shipped, Satya Nadella had already killed Windows Phone internally despite the Nokia acquisition he would later write-off that year in a $7.6 billion step backwards.

I predicted that Microsoft would miss its one billion milestone projection. And then it happened. In July 2016, one year after releasing Windows 10, Microsoft used a patsy to admit to its defeat: It would not meet its publicly-stated goal of getting Windows 10 on one billion devices in three or fewer years. And that patsy buried this news at the end of a 2000+ word post to help the company save face], which I nicely called out both graphically and in written form. Windows 10 would, of course, go on to hit the one billion milestone, though it took five years.

Terry Myerson wouldn’t be around to celebrate that. He was let go in 2018, and we later learned that his one billion milestone pledge was tied to a massive bonus, and so he had fudged the numbers in trying to hit the target. Terry, like Windows 10, was complicated.

Were Windows Phone successful, One Windows and the universal app platform might have made some sense. But with the loss of a phone and the feeble sales of Surface Hub, HoloLens, and Xbox One, Windows 10 was what Windows always was, a software platform for the PC. And in time, Microsoft scaled back its ambitions, replacing that universal app platform in Windows 11 with WinUI 3 and the desktop-focused Windows App SDK. The dream was over.

? Telemetry

When Steven Sinofsky led the Windows team, he started one trend that would in some ways become his most enduring legacy: He relied on telemetry, automated usage metrics supplied by the operating system, instead of customer feedback, to determine how to improve the product. When he revealed that Media Center would no longer be installed by default, for example, users who loved that app complained, but he pointed to telemetry that showed almost no one even launched that app, and of those who had, most were mistakes and the user quickly closed it.

There’s a largely apocryphal story claiming that Terry Myerson fired the entire Windows test team to save money because the Windows Insider Program that also started with the first pre-release version of Windows 10 would give the company all the testing it would need, and for free. This isn’t exactly true, and it’s unfair and untrue that Microsoft no longer tests Windows internally as well as externally.

But Microsoft’s use of telemetry did take a new and darker turn with Windows 10. Tied to Windows as a Service and the free upgrades and updates, Windows 10 would be the first Windows version to require consumer customers–individuals–to send some amount of telemetry data to Microsoft’s servers so that the company could quickly identify and fix widespread problems. This behavior wasn’t just controversial; it was a bridge too far for many users.

In Windows 10 version 1607, which shipped one year after the initial release, Microsoft tried to address complaints by engaging in what I called privacy theater. That is, it didn’t turn off or scale back the telemetry collection. Instead, it provided a byzantine set of privacy controls in Windows 10 Settings and Setup, giving users the illusion of choice. It introduced two settings, initially called “Diagnostics” and “Tailored experiences with diagnostic data,” that let users opt-in to more data collection and privacy violations.

The uproar was immediate. But those two settings, and Microsoft’s collection of data in Windows, continue on without meaningful changes today. This despite complaints from regulators in France, The Netherlands, the EU, and elsewhere. Telemetry data collection is somewhat defensible–the needs of the many outweigh the needs of the few, and so on–but it’s also just one form of privacy concern that began with Windows 10. And on that note…

? Privacy is relative

Privacy is one of those hot-button topics that always seems to bring out the crazies, with the overblown nonsense reactions to the Recall feature in Copilot+ PCs being only the latest example in our community. But Windows 10 was a watershed moment for Windows and privacy. And Microsoft did not handle this well.

The complaints were immediate. Right after Microsoft released Windows 10 in July 2015, I was forced to counter Windows 10 FUD (fear, uncertainty, and doubt) in my Short Takes column.

“With Windows 10 launching this week, the nutjobs have come flying out of the woodwork spouting nonsense, all of which, happily, is easily refuted,” I wrote at the time. “First, we were told that Microsoft’s ‘free’ Windows 10 upgrade would come with subscription fees after 2-4 years, despite what Microsoft was saying. Nope: Windows 10 is free, not ‘free.’ Then, we were told that a new Windows 10 feature (really a feature that debuted last year in Windows Phone 8.1) called Wi-Fi Sense would secretly let your PC share your secret Wi-Fi passcodes with friends. Nope: Wi-Fi Sense is opt-in and requires Windows 10 devices; no sharing of codes ever happens. And now we have the best one: privacy nuts are on fire because of a clause in the Windows 10 EULA, which supposedly states that ‘you give Microsoft very broad power to collect things you do, say and create while using its software [and that] Windows 10 will be reporting back many things that you do, to the Microsoft servers back at Redmond.’ Guys, seriously. Use Linux if you must. But don’t drag down the rest of us with your nonsense.”

One week later, I wrote a more serious article about the “overblown” privacy complaints surrounding Windows 10.

“Most of the complaints fall into two basic categories: those things that are in fact not new to Windows 10, and those things that are really new but are being overblown by privacy fanatics,” I noted. “Regardless, these reports are tugging at our very human tendency to see conspiracy where there is none: Windows 10 is free for many, so Microsoft simply must be doing something underhanded as a result. ”

The complaints boiled down to settings sync with Microsoft’s servers, Cortana data collection, features that “stole” Internet bandwidth, the unique advertising ID that Microsoft assigned to each PC for tailored ads (now common mobile platforms as well), and that Wi-Fi Sense nonsense. But none of these identified real privacy issues in Windows 10. I explained how to configure those privacy settings one could configure in Windows 10 at the time. But the privacy nuts were in a frenzy.

This is why Microsoft changed Windows 10 Setup, as noted above. This did absolutely nothing to address a single privacy issue in the system. But it worked: Regulators backed off, and the privacy nuts moved on to whatever other outrage. Only to return when Microsoft announced Recall. Welcome back.

? You’re getting Windows 10! And you’re getting Windows 10!!

Windows 10 was also controversial for several early incidents in which PCs would automatically upgrade to the system even though the user hadn’t authorized it. Some of this was literally mistakes tied to human error. But it did feel nefarious, and Microsoft was accused of using dark patterns to convince people to upgrade and then more aggressive malware-like behaviors, like preloading the upgrade on PCs without informing the user. The problem was so pronounced that third-party apps like Never10 appeared to help suspicious users avoid the unwanted upgrade.

I described this dark time as Upgradegate. But Microsoft eventually got past these issues, by adjusting how it prepped PCs for the upgrade and by being more explicit in clear when it did offer the upgrade. Thinking back on this now, it’s clear that the only real issue here was Windows 7. Those on Windows 8 mostly had few issues with this upgrade. But Windows 7, like Windows 10 today, had lots of holdouts.

⏹️ A user interface fit for a phone

As a user, the biggest problem I had with Windows 10, and it feels even more exaggerated today, is its user interface. Perhaps not surprisingly since Terry Myerson and his team had gained control of Windows after leading Windows Phone, Windows 10 featured a flat, squared off user interface that mimicked that created previously for Windows Phone.

Visual similarity and the resulting familiarity it brings is an understandable goal. It’s why Apple is getting so much press this year for bringing its Liquid Glass user interface to all its platforms. And Microsoft had previously used panoramic interfaces, albeit in a less widespread manner, across Windows RT tablets and Windows 8 PCs. But this UI never made sense on a PC.

The flat, squared off UI elements aren’t the issue. Yes, they look dated today, but they don’t impact the use of the system. The issue is phone features like Live tiles and Cortana that feel natural on a phone but are inefficient if not pointless on a PC.

Microsoft introduced Live tiles to Windows with Windows 8/RT, of course, and it solved a problem Windows 10 later did not by offering a full-screen Start experience in part so that users could take advantage of the very point of Live tiles, they’re ability to display live, “at a glance” information. That is instead of a static icon that could, at most, display a small status overlay, apps in Windows 8/RT (and 10) would use richer, bigger Live tiles.

Users rejected the full-screen Start experience, and so Microsoft returned the traditional Start menu to Windows 10. That was good for all the obvious reasons, but it also meant that the Live tiles it displayed couldn’t be used effectively. After all, the Start menu isn’t open and visible most of the time. And so those live, at a glance displays were wasted. And ignored. And finally removed in Windows 11.

Ditto for Cortana, a voice-activated digital personal assistant the likes of which made plenty of sense (at the time) when you were out in the world with your phone and could interact with the device using natural language. But Cortana proved unpopular on PCs for the same reason that most ignore touch screens and tablet form factors: PC users prefer the traditional PC interfaces and form factors that are better suited to productivity work. Few were interested in gabbing with their PCs.

We’re starting to replay that latter story today thanks to the rise of AI chatbots like Copilot and ChatGPT. But I suspect that history will simply repeat itself. Yes, many will interact with these chatbots using their voice on phones and other mobile devices. But when it comes to the PC, they will mostly type if they engage at all.

?It’s all about trust

If you’re familiar with U.S. history and politics, you may know or believe that the tumultuous events of the 1960s and 1970s, from the escalations of the pointless and unwinnable Vietnam war to the assassinations of John F. Kennedy, Robert F. Kennedy, and Martin Luther King, the Watergate scandal, and all the resulting protests of each, forever changed America, and for the worst. As a country, this is when we lost trust in our government.

Windows was, in many ways, the catalyst for a similar mistrust in Microsoft and Windows. It wasn’t the start–there were issues with Windows Vista, of course, and then with Windows 8–but these problems escalated dramatically in Windows 10 thanks to the telemetry, escalating ads, sponsored crapware advertising, forced upgrades, the reliability issues and then constant updating triggered by Windows as a Service, and the admittedly overblown privacy controversies.

(Those deeply involved in Windows during this time will also point to all the lies and half-truths around features that were promised but never delivered. Yes, this was all pretty terrible. But I wanted to focus on the issues that impacted everyone.)

Windows 10 also wasn’t the end of these issues. All the problems introduced in Windows 10 are magnified in Windows 11, and it is not coincidental that we now have a term, enshittification, that perfectly describes these behaviors. If Windows 10 was the start of the broad enshittification of Windows, and it was, then Satya Nadella is accurately described as the architect of this enshittification. His requirement that Windows adapt to his focus on the cloud was the biggest step ever, in the history of the platform, in undermining our trust.

As I’ve written so many times, trust is difficult to win but all too easy to lose. And once you’ve lost trust in something or someone, getting it back is the all the harder. I celebrated Windows 10 for its return to desktop-centric computing in 2015, but my trust in Windows declined over its lifetime and into the Windows 11 era. This feels avoidable and unnecessary. But it’s an important part of the history, and something to keep in mind if you’re somehow mourning the passing of Windows 10.

Whether Microsoft is repeating the mistakes of this past with Windows 11 and AI is debatable. Though I know some feel strongly negative about this, I don’t see it, given how well AI’s broad productivity capabilities map to specific Windows features. But I’ll check back in a few years and see if anything has changed. It’s possible that my final takeaway from the Windows 11 years will be as troubling as I now find Windows 10.

I hope not.