The history of Windows: How the OS has changed over time

By Kunal Khullar and Anita George Updated August 1, 2025

What comes to mind when you look back at the history of Windows? Is it the iconic logos, the ever-changing Start menus, or maybe the introduction of Live Tiles? The story of Microsoft’s flagship operating system has all of that and a whole lot more. Over the past 40 years, Windows has been reinvented time and time again. There have been a ton of different versions, and in this guide, we’re going to take a closer look at 15 of them that each mark a major milestone in the development of Windows.

Before we jump into the history of Windows, let’s take a look at what the state of computing was like before Windows.

Windows might seem like it’s been around forever, but it hasn’t. Windows was not Microsoft’s first OS. In fact, before Windows ever came along, PCs were run by another OS known as MS-DOS. Unlike even the first version of Windows, navigating your PC with MS-DOS was time-consuming, required the manual input of text commands to get anything done, and didn’t allow for multitasking (the ability to run multiple programs at once).

Windows, at least in 1985, wasn’t so much a brand new OS as it was a solution to the complications that an OS like MS-DOS presented. Windows 1.0 was created to be a graphical user interface (GUI) to be placed on top of MS-DOS, which made PCs that ran MS-DOS easier to navigate — it’s easier to look at a screen and click an icon to open a program than it is to type several commands just to complete the same task.

Windows wasn’t the first GUI created to solve issues like having to navigate via text commands, though. Two other companies got there first: Apple and Xerox. According to Wired, Apple released “the first commercial computer with a graphical user interface” in 1983. It was known as the Lisa. While the Lisa was the first commercial computer with a GUI, it still wasn’t the first computer ever with a GUI. The first one ever was introduced by Xerox in 1981, and it was known as the Star.

While Microsoft was late to the GUI party by about three or four years, it was able to sell its first version of Windows at a much more affordable price than its competitors, giving it a significant advantage.

This is the version that started it all. Windows 1.0 debuted in 1985 and was designed to be a GUI to be used in conjunction with MS-DOS. The use of Windows 1.0 as a GUI meant that MS-DOS users didn’t have to manually enter text commands just to complete basic tasks. Now, they could carry out tasks and browse their own files by just pointing and clicking on icons and menus. At the time of its release, Windows 1.0 cost $99 and introduced many computer users to drop-down menus, icons, and dialogue boxes. According to Microsoft, it also featured the ability to multitask applications and “transfer data between programs,” a first for a Microsoft OS.

Don’t let the bare-bones aesthetic of Windows 1.0 fool you — as The Verge notes, Windows 1.0 also came with a number of programs, including Windows Write, Windows Paint, a clock, a calendar, a notepad, a file manager, a cardfile, a terminal application, and even a game called Reversi.

It wasn’t long before Microsoft released a successor to its first GUI-enhanced OS. Just two years later, in 1987, the technology company released Windows 2.0. This version of Windows included such notable features as overlapping windows, resizable windows, keyboard shortcuts, and support for VGA graphics. The first Windows versions of Word and Excel also made their debut with Windows 2.0.

Microsoft’s next major milestone came with its release of Windows 3.0. This version of Windows is widely considered to be the start of Windows’ worldwide popularity as a desktop OS. Windows 3.0 came out in 1990 and offered 256 color support. More importantly, as PCMag notes, it featured “multitasking DOS programs,” which may have contributed to Windows’ surge in popularity. Another notable feature of Windows 3.0 is that it’s the version that saw the first appearance of the classic desktop game Solitaire.

A mere two years later, another OS update appeared, upgrading Windows to one of its most iconic versions, 3.1. The decimal in its name may make it sound like it was just a minor update to 3.0, but it wasn’t. Instead, in 1992, Windows 3.1 delivered quite a few new and essential features, such as support for TrueType fonts, the ability to drag and drop icons, and support for OLE compound documents (documents that combine elements from different programs). Also, according to The Guardian, it’s also the first version of Windows to have been distributed via CD-ROM.

When you think of the most iconic version of Windows, you’re probably thinking of Windows 95. That’s because it was such a huge departure from previous versions of Windows and aesthetically-speaking, and it set the tone for what we’ve come to expect from the Windows OS. As its name suggests, Windows 95 came out in 1995. It was the first 32-bit version of Windows (previous versions had been 16-bit), and it brought quite a few new features that ended up becoming historic additions. These include the taskbar, the Start menu, long file names, and plug-and-play capabilities (in which peripheral devices only needed to be connected to a PC in order to work properly). Windows 95 also saw the introduction of Microsoft’s web browser, Internet Explorer.

Another significant feature? Though Windows 95 still worked in conjunction with MS-DOS, as PCMag notes, unlike its predecessor, Windows 95 didn’t have to have to wait for the PC to boot into DOS first. This version marked the first time Windows was allowed to boot directly.

This is yet another version of Windows with a name that indicates the year it was released. If Windows 95 (eventually) brought us Internet Explorer, then Windows 98 strengthened the web browser’s grip on Microsoft’s OS. Indeed, this version of Windows not only brought us Internet Explorer 4.01, but it also delivered a slew of other internet-based programs and tools, such as Outlook Express, Microsoft Chat, and the Web Publishing Wizard.

Windows 98 also came with increased support for USB devices and Macromedia players (Shockwave and Flash).

Windows 2000 had a real focus on accessibility and introduced a laundry list of features to the OS, including StickyKeys, a high-contrast theme, Microsoft Magnifier, an on-screen keyboard, and a screen reader known as Microsoft Narrator.

Windows 2000 also delivered the Multilingual User Interface, which allowed users to choose the language in which their display would be viewed. Windows 2000 users could choose from a variety of languages, including Arabic, Japanese, and Greek.

The “ME” in Windows ME stands for “Millennium Edition.” It was also known by another, less flattering moniker: The Mistake Edition. According to PC World, Windows ME earned that nickname when it launched in 2000 because “users reported problems installing it, getting it to run, getting it to work with other hardware or software, and getting it to stop running.”

Despite its rocky start, it still managed to give us a useful tool: System Restore, a recovery feature that, in the event your computer starts having problems due to a poorly executed installation of a program or update, could remove those updates and restore your computer back to how it was before the offending update messed with your computer. In true Mistake Edition fashion, though, System Restore had its own issues to grapple with before it became truly great. For example, it sometimes bungled the restoration process by restoring things like malware that had already been removed.

Windows XP was released in 2001 and is widely considered to be among the great versions of Windows that Microsoft had to offer. There were two main versions of the OS: Home and Professional. Home was for personal use, and Professional was geared toward being used in work settings. As TechRadar notes, part of XP’s success can be attributed to the fact that XP launched right around the same time that there was a sudden increase in PC sales, and so for many new users, “Windows XP was just what came on their first computer.”

Some of XP’s popularity can be traced to the OS itself. After all, something had to be pleasing about its design if it ran for 13 years until Microsoft finally ended support for it in 2014. Some of its commercial success is because it is truly designed to be consumer-friendly. Its warm and inviting aesthetic is well-known: Bright colors, a happy green Start button, and customizable themes finally came standard with this version of Windows. It also came with new features, like native CD burning software, desktop search, remote desktop, and (eventually) improved security.

Vista was, unfortunately, another widely panned version of Windows. Vista was released in 2007, and one of the biggest sticking points was that its newly designed interface (known as Aero Glass) didn’t necessarily mesh well with older hardware or certain graphics drivers in newer PCs. Other criticisms of Vista included slow performance, overpriced, system resource consumption was too high, and, while the User Account Control feature kept you secure, the constant dialog boxes it generated were annoying.

Vista tried to accomplish too much too fast and got burned for it. It did introduce some helpful features, though, like Windows Defender, DirectX 10 (for PC gaming),  speech recognition, and Windows DVD Maker.

Two years later, Microsoft came back with a new version of Windows, known as Windows 7. Microsoft had to make up for Vista’s failures and was able to do just that with Windows 7. Compared to Vista, Windows 7 is a bit more streamlined, and it actually removed many features from previous versions of Windows, including Vista. In fact, there were at least four Vista programs — Windows Photo Gallery, Windows Calendar, Windows Movie Maker, and Windows Mail — that Microsoft did not include in Windows 7.

Windows 7 did, however, come with things like handwriting recognition, faster overall performance, interactive thumbnail previews for minimized app windows, a desktop slideshow feature, Internet Explorer 9, and Windows Media Player 12.

Visually-speaking, Windows 8 was radically different from its predecessors. It’s time to talk about that tile-filled Start screen. The Start screen featured tiles known as Live Tiles that acted as animated app shortcuts, which allowed you to open your apps and also displayed mini-updates about your apps (such as the number of unread messages). The Start screen was supposed to take over the role of the Start menu. In this setup, the traditional Windows desktop still exists in Windows 8, and it’s still where apps are run.

While not everyone was thrilled by the tablet-focused overhaul of Windows 8, it did offer a few other features, such as the ability to log in with a Microsoft account, support for USB 3.0, an actual lock screen (visually similar to a smartphone lock screen), and Xbox Live integration.

That jarring Windows 8 Start screen and removal of the Start menu wasn’t particularly well-received by consumers. In response, Windows 8.1 was released as a free upgrade to help address the concerns customers had about its predecessor.

Some of the corrections Microsoft made in Windows 8.1 included having an actual Start button on the taskbar again and letting users see the desktop first after logging in (instead of being greeted by the dreaded Start screen). It didn’t take long for Microsoft to issue this corrective version of Windows: Windows 8 was released in 2012, and Windows 8.1 was released in 2013.

Windows 10 came out in 2015 and was undoubtedly the most popular iteration of Windows. When it debuted, it was apparent that Microsoft wanted to refine its use of Live Tiles rather than get rid of them altogether. In Windows 10, it compromised: It got rid of the unloved Start screen from Windows 8 and replaced it with a larger Start menu that features the use of Live Tiles, among other kinds of app icons. It worked.

Other features that came with Windows 10 included the introduction of Cortana, a native digital personal assistant; the ability to switch between tablet and desktop mode; and a new web browser (Microsoft Edge), as per the Verge. Notably, support for Cortana was phased out in 2023 as Microsoft pushed towards AI-driven solutions like Microsoft Copilot. 

Windows 10 has also received fairly frequent updates since its launch in 2015 called Feature updates, which happened every six months. They were always free and available within Windows Update. Eventually Windows 10 also got UI improvements including redesigned icons and improvements to the Settings app, enhancing the overall user experience.

A version of Windows 10 specifically for ARM processors was also introduced, though it did not gain much traction. Microsoft will suspend free support for Windows 10, including security updates on 14 October 2025. While the operating system will still function, it will be more vulnerable to security risks. Organizations and individuals can choose to enroll in a paid Extended Security Updates (ESU) program to receive critical and important security updates for a limited time beyond the end-of-life date. 

Microsoft introduced Windows 11 in October 2021, marking a new era for its operating system with a significant visual and functional overhaul. It is the current iteration of Windows and recently surpassed Windows 10 as the most dominant desktop OS platform in the world. The most noticeable change introduced with Windows 11 was the redesigned user interface including a centred Start Menu and taskbar which faced a lot of backlash eventually forcing Microsoft to offer a quick setting change the its position as per the user.

Beyond the initial release, Microsoft has continued to evolve the OS with annual updates, introducing AI-powered features like Copilot and consistently improving security. Other changes included rounded corners, modern translucent aesthetics and enhanced productivity with features like Snap Layouts for better multitasking and direct integration of Microsoft Teams and Xbox gaming features.

Another key milestone for Windows 11 is its ability to run Android apps, bridging the gap between mobile and desktop experiences. The Microsoft Store was also completely redesigned to be a more unified hub for a wider variety of apps and even other third-party stores.

Windows 11 also introduced emulation for 64-bit (x64) applications, solving a major limitation of its predecessor and making ARM-powered devices vastly more capable. This coincided with the arrival of powerful new ARM chips, like Qualcomm’s Snapdragon X series, designed to rival Apple’s M-series processors in both performance and battery efficiency. This hardware push is central to Microsoft’s AI PC vision, using the powerful Neural Processing Units (NPUs) in these chips to efficiently run AI-based tasks including expanded for Copilot+ PCs.

Windows 11 represents a forward-looking step, adapting to the needs of a modern, hybrid workforce with a focus on a more personal, productive, and secure computing environment.

While Windows 11 continues to evolve with significant annual updates, the industry is already looking ahead to what’s widely rumored to be Windows 12. Though Microsoft remains tight-lipped, a consistent stream of information from industry insiders and even hints from Microsoft’s own presentations suggest the next generation of Windows will be built on three core pillars — Artificial Intelligence, deeper cloud integration, and a more modular design.

The most significant shift will be the further integration of AI throughout the operating system, going far beyond the current Copilot assistant. The vision is for an OS that is more predictive and personalized, with AI features that are context-aware, assisting with everything from file organization to system settings. This will likely be powered by a new generation of PCs with dedicated Neural Processing Units (NPUs) to handle these AI tasks efficiently without bogging down the main processor.

Leaks have also pointed to a potential redesign of the user interface, possibly featuring a floating taskbar and a more modular approach to the OS itself. This CorePC concept would allow Windows to be more adaptable to different devices, from powerful desktops to lightweight tablets, by only installing the necessary components. This could lead to a leaner, faster, and more secure operating system.

As for a release date, nothing is certain. Initial rumors pointed to a 2025 release, however Microsoft has confirmed that the next major update to Windows 11 would be the 25H2 update which is due to arrive later this year. The current consensus for Windows 12 is a 2026 release, although we believe that could be pushed further into 2027 or even 2028, depending how quick the AI is adapted withing the operating system.