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Windows 7: the golden child, the operating system that managed to charm both crusty IT veterans and fussy home users alike, wasn’t just good—it was unsettlingly good. So good, in fact, that many even now look upon their old, unsupported Windows 7 machines with the same muted sorrow as they might reserve for a beloved classic car that’s been banned from the road. Yet, as is the way with all things shiny and reputable in tech, Microsoft couldn’t just leave well enough alone. Enter, with a somewhat less triumphant fanfare: Windows as a Service.

From Beloved One-Offs to Eternal Upkeep: Why the Change?​

Let’s get one thing clear from the outset: Microsoft’s pivot from standalone, paid upgrades to the Windows as a Service (WaaS) model was not exactly an act of pure digital generosity. As Dave Plummer—one of Microsoft’s own former engineers and Task Manager’s unsung hero—so gently puts it: “when the product is free, the product is probably you.” Translation: if you thought Microsoft gave up its treasure chest of upgrade fees out of the goodness of its corporate heart, I have a bridge in Redmond to sell you.
Microsoft, you see, was a company under siege. By the time Windows 7 was winding down, Windows 8 had… well, it had happened. I won’t belabor the collective trauma that was that particular UI experiment. Meanwhile, Apple started handing out free macOS upgrades like Oprah on a sugar rush, and Linux suddenly seemed less like a bomb-defusal simulator and more like an actually usable operating system for everyday people. Even worse (from Redmond’s perspective), PC sales were drooping and the days when a new version of Windows meant a flood of cash had dried up.
And so, in a swirl of market panic and cloud-conversion zeal, Microsoft decided to give away Windows 10 as a free upgrade—not just to upstanding license holders, but even to those running slightly shadier copies of Windows. The idea? Give people the OS and earn revenue in new, recurring ways.
Now, for IT pros, this was both miraculous and suspicious. The hope of no more upgrade extortion was real—but what’s the catch? Spoiler: there were several.

Becoming the Service: Life on the Windows 10 Carousel​

On paper, WaaS sounded blissfully simple. No more massive, disruptive OS upgrades every few years. Instead, steady streams of updates to keep everyone on the latest and (supposedly) greatest version. Enterprises would never have to justify a giant OS rollout again, home users wouldn’t be left out on unsupported islands, and everyone would get all the shiny features Microsoft’s devs could dream up, delivered on an endless slow-burn release cycle.
In reality? The experience for IT admins sometimes felt reminiscent of Sisyphus—except instead of rolling a boulder up a hill, it’s feature deferrals, update rings, and hoping nothing explodes the next time Patch Tuesday rolls around. Sure, the update mechanisms got better, but let’s be honest: WaaS meant IT had to keep learning new tools, new jargon, and stay forever on alert for what got quietly deprecated along the way.
But it’s not just the admins who felt the tickle of Microsoft’s new strategy. With WaaS came a bonanza of telemetry. Windows 10, rebuilt from the ground up, phoned home with a frequency that would have made your average 1970s espionage agency blush. Ostensibly, this was for our own good: anonymous diagnostics, error logs, improvement suggestions—who wouldn’t want their OS to get smarter over time?
Of course, ask enough users, and the answer turns out to be: “lots of people.” For them, “anonymous telemetry” sounded less like peaceful progress and more like being quietly followed around a shopping mall by a very enthusiastic personal shopper who just won’t leave.

Ads, Upsells, and the Evolving Windows Experience​

But wait! The brave new service-era Windows was supposed to not just silently study you—it started talking to you, too. With ads. In your Start Menu. And taskbar. And pretty much anywhere else that historically had been a calm, ad-free refuge. It was no longer enough to be a captive user; now, Windows wanted you to visit the Microsoft Store, try Edge, and maybe, just maybe, pony up for a little Bing or Office 365 magic on the side.
Once upon a time, updating Windows improved your computing life. Now, updating Windows sometimes meant getting a new “suggested app” or a pop-up gently needling you to stop using Chrome. It felt kind of like returning home after a trip, only to find a cheerful salesperson waiting in your kitchen, explaining the features of your own refrigerator and quietly suggesting you try their new line of condiments.
For enterprise users, the issue became more than an annoyance. Ads in Pro and even Enterprise SKUs felt like an outright cheeky move from Microsoft. As Plummer himself laments, if you pay for a professional OS license, shouldn’t you get to skip the sales pitch? Should your hard-earned outlay get you peace, or does it just buy you a slightly more refined form of being “monetized”?

Telemetry: Friend, Foe, or Frenemy?​

Telemetry is one of those topics that divides the community more sharply than tabs versus spaces (and trust me, that gets heated). Microsoft’s pitch is straightforward: mass telemetry lets them see what’s working, what’s breaking, and what’s driving users to shout into the void on tech forums. In theory, more data means a better OS for all.
In practice, however, “telemetry” still means “someone else’s computer is watching what I do.” Even if it’s anonymized, even if it’s for product improvement, many users (and plenty of IT leaders) are uneasy with this baseline level of digital observation. Worse, the settings for turning telemetry off are famously labyrinthine, and IT admins often need to deploy group policy objects, registry hacks, and the odd exorcism just to keep curious packets from heading Redmond’s way.
And that’s just the home and Pro editions—Enterprise users get slightly more granular controls, but nothing like “off means off.” The feeling is a mix of resignation and irritation: you’d think shelling out for a corporate license would buy you a little privacy, but alas, the meter’s always running.

The Revenue Buffet: Serving Ads, Smoothing Spikes, and Taming Pirates​

For Microsoft, the elegant beauty of WaaS isn’t just a steadier update process—it’s a smoother, more predictable income curve. Windows as a Service spreads out the feast (and famine) of revenue that used to spike around big launches. Between OEM device sales, subscriptions for add-ons (think OneDrive, Microsoft 365, and more), and the occasional in-OS upsell, Microsoft can keep the cash rolling in even as consumers hold onto hardware longer.
One genuinely clever aspect: piracy reduction. Microsoft realized it was easier to fight pirates with honey than lawsuits. By offering Windows 10 even to users with “non-genuine” copies, they could migrate illicit installs into the official, upgradable user pool—potentially turning freeloaders into customers of the Windows Store, the default browser, or cloud services. If anything, this strategy is less “fighting piracy” than “raising the stakes of the free-to-play game”—convincing users that being legitimate can be almost as convenient as playing fast and loose… provided you’re okay with constant reminders about Microsoft’s branded bounties.

Real-World IT: The Never-Ending Windows Road​

What does this all mean for IT professionals? Consider this your new normal: a constant process of testing, validating, scheduling, and praying about updates. No more nice long rests after a version migration; WaaS means the treadmill of feature updates never stops. Windows Insider channels, release rings, testing environments—these aren’t just nice-to-haves, but required to stay even remotely ahead of the game.
On the plus side, patching critical vulnerabilities is faster, and security hygiene, in theory, is vastly improved. But you won’t find many who’d call the pace “relaxing.” User pushback is real—from surprise restarts to mysterious new interface elements, IT finds itself dealing not just with tech, but with expectations management and reality-checking rumors that emerge with every new build.
And here’s where Microsoft’s “as a Service” rhetoric gets a little squirrelly. As a product, Windows was something you owned, tamed, and rolled out on your terms. As a service, it’s something you rent, wrangle, and increasingly find yourself adjusting to—often in ways that favor Microsoft’s own business interests just as much as your own.

The Cloudier, More Lock-In-Prone Future​

The movement toward WaaS dovetailed perfectly with Satya Nadella’s reign and Microsoft’s grand pivot from Windows-first to cloud-and-engagement-first. It’s not just about updating the local OS anymore—it’s about connecting you to a suite of Azure-driven and Microsoft account-tied services. Windows is now a staging area for a much larger range of revenue opportunities.
Every small “suggested” app or “Try Edge!” nudge is ultimately about herding users into Microsoft’s broader subscription-and-service ecosystem. From OneDrive and Teams to Windows Copilot and Bing Chat, Windows is less a destination than the on-ramp for a much richer (read: recurring-revenue heavy) journey.
From an IT risk perspective, the potential for lock-in only grows. Choices get narrower, default integrations become harder to disentangle, and cross-cloud compatibility more fraught. The price for seamless “engagement” is flexibility. Vendors know it—and the more deeply tied your identity, data, and workflows are to their platforms, the stickier the relationship becomes.

The Case for an Ad-Free, No-Telemetry Windows (and Why It’ll Be Hard to Get)​

This, perhaps, is the fundamental gripe articulated by Plummer and echoed by countless professionals and enthusiasts: With so much value being extracted from user data, ads, and up-sells, why can’t those willing to pay for a “pure” Windows experience get it? As Plummer puts it, “I for one would gladly pay $10 or maybe even $20/month for a version of Windows Pro that included no telemetry or unnecessary telematics.” Many in IT would agree—if anyone is willing to pay for dignity, privacy, and a little peace, it’s the folks who manage fleets of machines.
Yet so far, Microsoft has kept even high-tier versions on a single track. Sure, you can mute some upsells and set data collection to “minimal,” but total privacy? Not on the menu. The inescapable reality: Microsoft’s long game is about more than licenses. It’s about participation in their ever-deepening digital economy, where data—yours and your users’—stays the secret sauce.

Examining the Competitive Landscape: A Cross-Platform Reality Check​

It didn’t help, of course, that while Windows grew ever more monetized, Apple and Linux were busy advertising their OSs as “free” (albeit with hardware or skillset costs clearly baked in). And, as Plummer now admits, switching between macOS, Windows, and Linux daily is a revelation. Where the Mac feels cohesive—if a little walled garden—the Linux desktop feels both empowering and, occasionally, experimental. Windows, on the other hand, sometimes feels like that trusty Swiss Army knife that’s quietly keeping tabs on which tools you use most—and suggesting a Microsoft-branded corkscrew every other Tuesday.
It’s not that Windows isn’t still powerful, flexible, or critical. It’s just that the cost of using it now includes a healthy side of nudges, nags, and data pings. For the IT industry, this means endless balancing acts: user autonomy versus convenience, privacy versus security, and freedom versus the ever-present gravitational pull of Microsoft’s sprawling digital orbit.

Conclusion: Welcome to the Windows as a Service Era—You’re Both the Customer and the Product​

So, as the dust of Microsoft’s pivot to Windows as a Service finally settles into a new status quo, what do we have? The answer is complicated: a more evergreen, more secure, but also more intrusive Windows. A landscape where upgrades are free, but privacy is a sliding, not absolute, scale. Where the adage “if you’re not paying for the product, you are the product” now rings as true for the world’s most popular operating system as it does for your average social network.
For IT pros, users, and enthusiasts: welcome to the future. May your GPOs be effective, your Start Menu unmolested by suggested apps, and your telemetry minimal—at least until the next update resets all your settings again.
And remember, next time your OS tries to upsell you a cloud service, just tell it you’re holding out for the “Pro No-Nag” edition. If enough of us ask, who knows: maybe some day, Microsoft will finally figure out what pro users have actually been wanting all along—a solid, quiet, ad-free Windows that simply gets out of the way, does its job well, and lets us be the customer. Until then, keep your Group Policies close, your registry edits closer, and your sense of humor closest of all—because Windows as a Service isn’t just a policy, it’s a lifestyle.

Source: theregister.com When Microsoft made the Windows as a Service pivot