On September 30, 2014, Microsoft announced Windows 10, an operating system that fundamentally changed the company's approach to one of its flagship products. As support nears its end, today it's an operating system that users are still holding on to, fighting Windows 11 with everything they've got. So it's easy to forget how absolutely crazy Windows 10 was as a concept.
On September 29, 2014, Windows 8 was the reigning disaster, and Windows Phone was still promising. Since then, the Microsoft Band has been announced and discontinued, and Windows 10 looks completely different than it did when it launched.
Microsoft had the same problem with Windows 7 as it did with Windows XP, an extremely popular operating system that very few people wanted to upgrade from. Windows 10 was an incredibly radical idea. Here's why.
6 HoloLens
It's like Apple Vision Pro, but much earlier and better
Microsoft held several events leading up to the release of Windows 10 on July 29, 2015. In January 2015, the company introduced HoloLens, its first holographic computer.
By today's standards, it's not crazy as there are different types of AR glasses everywhere. But when this thing was announced, it blew my mind. I remember showing the teaser video to everyone who wanted to see it. It was just so cool.
The idea wasn't too dissimilar to 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 rendering it full screen.
HoloLens never became a consumer product because HoloLens 2 was aimed squarely at enterprises. HoloLens 2 is now five years old and by all accounts the product is internally dead.
5 A free upgrade
Microsoft had always charged fees for Windows
In early 2014, Microsoft went through the ordeal of trying to kill Windows XP, an old operating system that people didn't want to let go of. The company faced a very real problem: every time it releases a new operating system, it competes with itself.
The solution was radical. Windows 10 should be a free upgrade for anyone using Windows 7, Windows 8.1 or Windows Phone 8.1. While only a small portion of the promised phones were upgraded, all Windows 7 and Windows 8.1 PCs had the option to upgrade, and the system requirements established with Windows 7 in 2009 remained (mostly) the same until Windows 11 launched in 2021.
Windows still wouldn't be free. You're still paying for it when you buy a new PC, and most people got upgrades anyway. And if you want 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.
4 The Windows Insider Program
We are all beta testers now
The guy on the left looks SUPER awkward
After the announcement in 2014, one of Microsoft's first moves was to introduce the Windows Insider Program, which allowed 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 largely similar to Windows 8, but had a normal Start menu.
The program was divided into two “rings,” the Fast Ring and the Slow Ring. One was intended for being the first to try new things, while the other was more for people who valued 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 would push new features so frequently that a stable slow ring build couldn't be achieved. When leadership of the Windows Insider program was transferred from Aul to Dona Sarkar, weekly fast ring builds and monthly slow ring builds were planned, but keeping the slow ring on schedule proved to be a challenge.
Eventually the program was switched to “channels” called “Dev,” “Beta,” and “Release Preview.” A Canary Channel was later added with even more frequent builds than the Dev Channel.
The Windows Insider Program also introduced the Feedback Hub, which prompted Microsoft to all but shut down its internal testing program and let Insiders do the work for free.
3 Windows as a service
Taking responsibility for updates
Windows 10 introduced the concept of Windows as a service, which essentially meant that Microsoft promised to service your PC until the end of the device's lifespan. This meant frequent feature updates and was also a commitment to free updates.
It also sparked some conspiracy theories. By this point, Office 365 was already out and people were starting to wonder 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 comments from prominent publications of the time and find some people absolutely promising that this would be Microsoft's plan to charge for Windows again. In fact, the idea of a free upgrade to Windows 10 was so radical.
Windows as a Service definitely had some hurdles along the way. Sometimes it seems like Microsoft is all too willing to push updates, sometimes with disastrous consequences. With Windows 10 version 1709 (known as the Fall Creators Update), the company skipped the release preview ring entirely and shipped it directly to consumers, but then had to pull out after users' files were lost.
Eventually, the semi-annual feature updates became annual, and Microsoft really scaled back the attempt to introduce wild new features with each update, as it did in the early years of Windows 10. What's new in Windows 11 version 24H2 isn't just brand new Copilot+ PCs? Not much.
2 Run pretty much any app
They were called bridges
I've already mentioned 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 big problem was Windows 8 disaster recovery, where some good ideas were implemented extremely poorly.
The Windows Store (now called Microsoft Store) was one of those things. OS Microsoft added one with Windows 8, but it was pretty terrible, only allowing apps that used the new Metro UI.
With Windows 10, the Store obviously supported Metro and UWP apps, but Microsoft had much bigger plans to allow developers to port apps and call them Bridges. Most of them are dead now.
It started with Project Astoria, which was supposed to make Android apps run on Windows. This only ran on Windows Phones in the preview era and was discontinued before general availability. Android apps on Windows have been revived with Windows 11 using a completely different method, but it will be retired in March 2025.
Next up is Project Islandwood, a plan that should 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 did not support the latest developments in iOS development such as the Swift language and was eventually open sourced and largely abandoned.
Project Westminster was a way to package hosted web apps, which you can still do more or less, although the tools have changed somewhat to support newer progressive web apps.
Project Centennial was a way to bundle classic desktop apps for the store. Back then, Microsoft was still trying hard to go beyond classic desktop apps. For this purpose, the company released the Desktop App Converter, and this tool is now deprecated as Windows 11 simply allowed anyone to put any Windows app in the Store.
But that's it. Microsoft's solution to the app gap was to simply let you run any app built for any platform. It was wild.
1 A Windows
One operating system that handles them all
This was less of a planned feature and more of a big vision behind Windows. It was easy. Eventually all Windows devices would run a version of Windows.
I've talked a lot about the problems Microsoft tried to solve with Windows 10. Another problem was that it suffered huge losses in mobile phones. So where did Windows win? PCs, of course. So if we just call Windows Phones small handheld PCs, that's successful now, right? Bueller?
It's more complicated. Continuum was an example of where you had a phone, connected it to a big screen, and had a desktop. Windows Mixed Reality was another. You would connect a headset to your PC and you would have the mixed reality shell. Even tablet mode was once called Continuum.
You get an operating system and a shell based on the screen you use. If this idea ever saw the light of day and we still had Windows Phones, they would use the Windows on Arm builds we see today, just with a smartphone case until you plug in another screen.
I thought about adding UWP to this list since it was just as crazy as everything else, but actually that was part of this One Windows concept. A true UWP app would be an app that runs 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.
Of course, UWP's value proposition begins to disappear as these different device types go away.
The One Windows approach was one of my favorite crazy ideas for Windows. Microsoft really shot for the moon with Windows 10, doing things it's never done before and finding unique solutions to a range of problems.
Honorable 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. Plus, Windows 10 S wasn't so much a crazy idea as a bad idea.
I like to call Windows 10 S the “gotcha” operating system. To compete with Chromebooks, Microsoft created a locked version of Windows 10 that only allowed you to get apps from the Store. It was actually assumed that people would like this too, although at this point almost no one could get a satisfactory experience just by getting apps from the store.
However, it differed from Windows RT in that you could upgrade from what would later be known as S mode for an additional cost. Understood.
Windows 10X was completely different. This was Microsoft's latest attempt to develop a modern Windows while getting rid of the legacy issues. It was introduced as an operating system for dual-screen and foldable devices, even if it wasn't intended for that internally. The dual-screen Surface Neo never shipped, and Microsoft announced that Windows 10X would be coming to single-screen devices instead. Windows 10X was eventually scrapped before it saw the light of day.