On September 30, 2014, Microsoft announced Windows 10, an operating system that fundamentally shifted the company's approach to one of its flagship products. As it nears the end of support, today it's an OS that users are still clinging to, resisting Windows 11 with everything they've got. So, it's easy to forget just how absolutely crazy Windows 10 was as a concept.
On September 29, 2014, Windows 8 was the reigning disaster, and Windows Phone was still showing promise. Since then, the Microsoft Band was announced and killed, and Windows 10 looks totally different from when it launched.
Microsoft was facing the same problem with Windows 7 as it had with Windows XP, an extremely popular operating system that very few people felt compelled to upgrade from. Windows 10 was an incredibly radical idea. Here's why.
6 HoloLens
It's like Apple Vision Pro, but way earlier, and better
Microsoft held multiple events leading up to the Windows 10 release on July 29, 2015. In January 2015, it introduced HoloLens, its first holographic computer.
It's not crazy by today's standards, with different kinds of AR glasses all over the place. But when this thing was announced, it blew my mind. I remember showing the teaser video to everyone that would look. It was just so cool.
The idea wasn't too dissimilar from what Apple has today with Vision Pro. It was a UI on top of the real world, except HoloLens actually showed you the real world instead of reproducing it on a full-screen.
HoloLens never became a consumer product, with HoloLens 2 being squarely aimed at enterprises. HoloLens 2 is coming up on five years old now, and by all accounts, the product is dead internally.
5 A free upgrade
Microsoft had always charged for Windows
Earlier in 2014, Microsoft was going through its ordeal of trying to kill Windows XP, an ancient operating system that people did not want to let go of. The company was facing a very real problem: every time it releases a new OS, it's competing with itself.
The solution was radical. Windows 10 was going to be a free upgrade for anyone running Windows 7, Windows 8.1, or Windows Phone 8.1. While it only ended up upgrading a small portion of the phones it promised to, all Windows 7 and Windows 8.1 PCs got the option to upgrade, and the system requirements set in 2009 with Windows 7 remained (mostly) the same until Windows 11 launched in 2021.
Windows still wasn't going to be free. You still pay for it when you buy a new PC, which was how most people got upgrades anyway. And if you wanted to install Windows on a new device, you still have to buy it.
In 2021, Windows 11 arrived as another free upgrade, at least for supported hardware. Every feature update since Windows 10 was released has been free of charge.
4 The Windows Insider Program
We're all beta testers now
After the announcement in 2014, one of the first things Microsoft did was launch the Windows Insider Program, allowing anyone to be the first to try out new Windows features. Led by Gabe Aul at the time, the first build was released the next day, on October 1, 2014. It was pretty much like Windows 8, but with a regular Start Menu.
The program was divided into two "rings", the Fast Ring and the Slow Ring. One was for being the first to try new things, while the other was made more for people that prioritized stability. Later, the Release Preview Ring was added for updates that were expected to be ready to ship.
There was a lot of trial and error with this approach. Often, the team was pushing new features so frequently that it couldn't land on a stable Slow Ring build. When Windows Insider Program leadership transferred from Aul to Dona Sarkar, the plan was for weekly Fast Ring builds and monthly Slow Ring builds, but it proved to be a challenge to keep the Slow Ring on schedule.
Eventually, the program shifted to having "channels", which were called Dev, Beta, and Release Preview. Later, a Canary Channel was added with even more frequent builds than the Dev Channel.
The Windows Insider Program also introduced the Feedback Hub, which Microsoft used as an opportunity to all but shut down its internal testing program and have Insiders do the work for free.
3 Windows as a service
Taking ownership over updates
Windows 10 introduced the concept of Windows as a service, which essentially meant that Microsoft was promising to service your PC until the end of the device's life. This meant frequent feature updates, and it was also a commitment to free updates.
It also sparked some conspiracy theories. By then, Office 365 was a thing, and people were starting to wonder just how many more perpetual license versions of the product there would even be. With Office moving to a paid subscription model, some suspected that Windows would do the same.
In fact, you can definitely Google some op-eds from prominent publications of the time and find some people absolutely promising that this was going to be Microsoft's plan for once again charging for Windows. In fact, that's how radical the idea of a free upgrade to Windows 10 was.
Windows as a service definitely had some bumps in the road. At times, it would seem like Microsoft was all too eager to push updates, sometimes doing so with disastrous consequences. With Windows 10 version 1709 (known as the Fall Creators Update), the firm skipped the Release Preview Ring completely and delivered it straight to consumers, but then had to pull back after users' files started going missing.
Ultimately, the semiannual feature updates became annual, and Microsoft really scaled back on trying to introduce wild new features with every update like it did in the first few years of Windows 10. What's new in Windows 11 version 24H2 that's not exclusive to brand-new Copilot+ PCs? Not a lot.
2 Run pretty much any app
They were called bridges
I mentioned earlier that one of Microsoft's biggest challenges at the time was that it was competing with itself every time a new version of Windows was released. However, another really major issue it had was recovering from the disaster that was Windows 8, which had some good ideas that were extremely poorly executed.
The Windows Store (now called the Microsoft Store) was one of those things. OS X, iOS, and Android all had app stores that you could use to obtain software, providing a trustworthy outlet. Microsoft added one with Windows 8, but it was pretty awful, only allowing apps that used the new Metro UI.
With Windows 10, the Store obviously supported Metro and UWP apps, but Microsoft had much grander plans to allow developers to port apps, calling them bridges. Most of these are dead now.
First up was Project Astoria, which was going to get Android apps running on Windows. This only ever ran on Windows Phones in the preview era, and it was killed prior to general availability. Android apps on Windows was revived with Windows 11 using an entirely different method, but that's being killed in March 2025.
Next is Project Islandwood, which was a plan to allow developers to recompile their iOS apps for Windows. The problem here was that it was never good enough for iOS developers to adopt. It didn't support the latest developments in iOS development like the Swift language, and was eventually open-sourced and mostly abandoned.
Project Westminster was a way to package hosted web apps, which you can still more or less do, although the tools have changed a bit to support newer progressive web apps.
Project Centennial was a way to package classic desktop apps for the store. At the time, Microsoft was still very much trying to move beyond classic desktop apps. The company released the Desktop App Converter to do this, and that tool has since been deprecated since Windows 11 just allowed anyone to put any Windows app in the Store.
But that was it. Microsoft's solution to the app gap was to just let you run any app made for any platform. It was wild.
1 One Windows
One OS to rule them all
This was less of a planned feature and more of a grand vision behind Windows. It was simple. At some point, we'd have one version of Windows running on all Windows devices.
I've talked a lot about the problems Microsoft was trying to solve with Windows 10. Another one was that it was losing big in phones. So, where was Windows winning? PCs, of course. So if we just call Windows Phones little handheld PCs, that's successful now, right? Bueller?
It's more complicated than that. Continuum was an example of this, where you'd have a phone, plug it into a big screen, and you'd have a desktop. Windows Mixed Reality was another. You'd plug a headset into your PC, and you'd have the Mixed Reality shell. Even tablet mode was branded as Continuum at one point.
You get one OS, and it you get a shell based on the screen you're using. If this idea ever saw the light of day and we still had Windows Phones, they'd use the Windows on Arm builds we see today, just with a smartphone shell until you plugged in another screen.
I considered adding UWP to this list since it was just as crazy as anything else, but really, that was a part of this One Windows concept. A true UWP app would be one app that ran on phones, PCs, VR headsets, HoloLens, Xbox, and anything else by simply adapting to the screen. The app was a single build with a responsive UI.
Naturally, the value proposition of UWP starts to evaporate when those different device types go away.
The One Windows approach was one of my favorite crazy ideas for Windows. Microsoft really just shot for the moon with Windows 10, doing things that it never did before and finding unique solutions to a range of problems.
Honorary mention: Windows 10 S and Windows 10X
Windows 10 S and Windows 10X came much later, so I didn't include them in the list. Also, Windows 10 S specifically wasn't so much a crazy idea as much as it was a bad idea.
I like to call Windows 10 S the "gotcha" OS. In an attempt to compete with Chromebooks, Microsoft made a locked down version of Windows 10 that only allowed you to get apps from the Store. It actually thought people would like this too, despite the fact that almost no one could get a satisfying experience by only getting apps from the Store at the time.
It was different from Windows RT though, because you could upgrade out of what later became known as S mode for a price. Gotcha.
Windows 10X was totally different. This was Microsoft's latest attempt to build a modern Windows, shedding legacy bloat. It was introduced as an OS for dual-screen and foldable devices, even if that's not what it was for internally. The dual-screen Surface Neo never shipped, and Microsoft announced that Windows 10X was coming to single-screen devices instead. Windows 10X was eventually scrapped before it saw the light of day.