Blog 3: Windows…a {quick} Retro

MS-DOS to Windows 11

Microsoft recently released a new version of Windows on October 5th, 2021. Windows 11 is going to be another major version of the Windows operating ecosystem. With the a new version coming out, I thought it would be interesting to look back at the release of past Windows OS releases.

Where did it all start?

The first version of Windows was released in November 1985 and dubbed, Windows 1. Windows 1 was built on MS-Dos and Microsoft’s first true attempt at a graphical user interphase (GUI) using 16-bit. I’m sure there are still a few of us that used MS-DOS including early versions of Windows. Sometimes I prefer using a system that has limited GUI…but I’m not sure if W1 would lend itself to the productivity levels I require today.

Microsoft Windows 1.04

The first major update…

Overlapping windows! Feedback from W1 gave way to overlapping windows in W2! Along with overlapping windows, users had access to a control panel where they could customize certain configurations. The unique aspect to this change was that all of the settings were brought together in one area. This update has survived the test of time and is still a feature of the Windows ecosystem.

Windows 2 showing overlapping windows and desktop applications

A bite out of Macintosh

Before Windows 3, Microsoft’s operating system did not require a hard drive. The launch of W3 required a hard drive in 1990 and was seen throughout the industry as competition to Apple’s Macintosh. Windows 3 introduced the ability to run MS-DOS programs in Windows allowing for what we now know as multitasking. Further, the GUI increased the color scale to 256 colors, drastically helping modernize the interface.

Windows 3.1, released in 1992 made personal computers easier and more fun to use and provided users two great transformations. First, TrueType fonts made Windows a viable publishing platform for the first time in it’s history. Second, Minesweeper made its first appearance to users. W3.1 required 1MB of RAM to run and also supported MS-DOS programs to be interacted with a mouse for the first time.

Windows 3.1

Windows 95; A BIG Microsfot Launch!

The start button…finally gets introduced in Windows 95! Named for the year it came out, Windows 95 introduced the Start button and Start Menu and Microsfot pushed the new technology hard via marketing campaigns…see below:

And if that didn’t get you jacked up… here’s a couple billionaires dancing to…the thought of Windows 95.

Not only was the Start button a major transformation, the entire launch of Windows 95 was by far largest update Microsoft had ever undertaken. Forbes says that this version of Windows is still the most significant launch Microsoft has ever launched and helped change the PC more than any version of Windows before or thereafter.

A brief overview of some new features Windows 95 included:

  1. Start button and taskbar – the Start button and task bar are one of the few items that Microsoft has never tried to remove from it’s software….yet.
  2. A true operating system – up until W95, Windows had been GUIs sitting over MS-DOS. W95 was the first real operating system that did true heavy lifting within the computer. For all you gaming fanatics, W95 played a huge role in being able to play video games on a PC (DirectX)
  3. Access to the Internet!
  4. Cloud computing…kind of – Windows “Briefcase” was cloud computing before cloud computing. Autosave feature on a disk was a new idea to computing and W95 included the ability to do this via Floppy Disk…So now you could take your files from computer to computer using a floppy disk. #revolutionary (I’m kidding about being cloud computing)
  5. User Profiles – the first time different profiles could log in to different profiles…neat!
  6. Plug & Play – Windows could now detect compatible hardware and install software automatically…something that Apple did not allow. Still to this day, it is arguably easier to connect older devices to a Windows PC than it is to connect anything to an Apple device. But…who even uses cords these days?

Windows 98 – Internet Explorer

Windows 98 was not a huge shift from Windows 95, but did add a few features that users enjoyed:

  1. Improved window UI– Windows 98 brought more gradient colors and gave a 3D effect border around a chosen menu item
  2. Microsoft Internet Explorer! Windows began integrating IE (for better or worse) to its Windows systems. IE not only displayed web pages, but also helped manage the help system in Windows. in 1998, IE became the world’s most popular browser in terms of market share, eclipsing Netscape Navigator. IE owned > 90% of browser market share until the early 2000s, but would hold on to be the world’s most popular browser until being surpassed by Chrome in 2012. Over a decade of market dominance…not too shabby Internet Explorer! (Chrome is by far the world’s most popular browser still)
  3. Quick Launch Toolbar – A toolbar that can integrate start menu and personalized shortcuts.
  4. “Show Desktop” Button – Such a useful tool I still use today…minimize everything, show just the desktop!
Windows 98

Windows ME – Millennium Edition

Well, Microsoft didn’t always hit big with their new operating systems. Sadly, this won’t be the first time the release of an OS goes poorly for Microsoft. However, it is worth noting that Windows ME was the last version of Windows to be based on MS-DOS…so that’s good.

Windows ME was supposed to make your home computer a “multimedia entertainment center. Internet Explorer 5.5, Windows Media Player 7, Windows Movie Maker all debuted in ME. Overall, ME was buggy, didn’t install property, and is all worth forgetting aside from noting that it’s tough to release new software and have everyone love it.

Windows 2000

The release of W2000 gave a way forward for Microsoft, especially after a disasterous experience with ME. Windows 2000 was originally intended only for business, but with ME crashing systems and being unusable, individuals pirated the business software to use on their personal PCs. While definitely illegal to do so, W2000 gave hope that a better system was coming for Windows users.

Windows XP

A golden era for Windows? One of the best Windows Operating Systems, released in October 2001, brought Microsoft’s enterprise and consumer lines of operating systems under one software package. For consumers and business people alike, this was huge. For the first time, the same computer that your enterprise company was using at work would look exactly the same as your computer at home. This made it easier for users to learn how to use the software and intricacies of their PCs.

The biggest upgrades for Windows XP were a new and updated color scheme, more practical interface, and improved application and memory management (i.e. no more crashing and buggy experiences). Windows XP’s user friendliness was a huge factor in its success. From internet browsing, using Microsoft Office products like World and PowerPoint, playing Solitaire, Windows XP was a fan favorite operating system because of it’s ease of use.

Windows XP was the longest running Windows operating system which included three major updates within XP. The operating system, released in 2001, was officially unsupported in 2014. Even when updates were no longer available for XP, enterprises continued to use XP because of it’s ease of use, so much so that it was estimated that 430 million PCs ran XP when it was discontinued.

Windows Vista

Windows Vista was released in early 2007 and came with a new look and feel compared to XP’s GUI. The operating system was noted to be more reliable and more stable compared to previous versions of Windows. After versions of Windows that lacked security, stability, and application compatibility, Vista was a refreshing release that gave those features to Windows users. However, if you had never used Windows ME, you may have thought Vista was the worst Windows released. With increased security came increased frustration and annoyances with the new Vista. User Account Control (UAC) was developed and prompted the user to approve any type of changes to the computer. Even when installing new editions of Microsoft software, UAC appeared and made the user agree to install the newest version of Word.

For a demonstration of what this actually felt like….cool guy Mac commercials highlighted it for us:

Windows 7

Vista, only three years old is replaced by Windows 7 (released October 2009) and introduced Microsfot Touch – giving more options to the user for how to interact with the software for those who used a touchscreen. One of my favorite featuers that Windows actually had beaten Mac at for some time was the ability to “snap” windows to the sides of the screen, allowing for fast multitasking. Mac has since released this on their OS, but Windows rolled this out in 2009.

Windows 8

Possibly the worst Windows, in my opinion. The colored tiles, the weird icons…none if it played for me. Where’s the start button?! A huge change away from Windows 7 for really no reason. And then they added in all the bloatware. I almost skipped Windows 8 because it’s making me angry just to think about.

Windows launched the Windows Store in Windows 8 as one of it’s many tiled pieces of software that came included in the operating system. Specific stores, at the time, were really only on OS devices. Now, Google, Microsoft, and Apple all host their own “stores” on their Operating Systems. In 2012 this was a new feature, but is one that has stuck around on Windows devices.

Overall, the new moving tiles, a radical change from the long lineage of Windows UI, and a move away from the start button are all reasons why I did not favor Windows 8…and I don’t think I am alone in that regard.

Windows 10

Windows 10 was announced in 2014 and became generally available during the summer of 2015. As computers shifted from being stationary to mobile and then from single-form to multi-form (laptop -> tablet) so too did the need for an operating system that fit. Windows 10 was built with the Surface Pro family in mind. Being able to switch between a keyboard and mouse and tablet mode was a new feature that Windows 10 handled…and Windows continues to handle quite well (I am writing this in desktop mode on a Surface Pro)

Windows 10 was a huge upgrade from Windows 8. Windows 10 combined the appearance of Windows 7 and live tiles from Windows 8. An “Action Center” was also introduce, which gives quick access to certain settings and notifications, very similar to the side panel of MacOS, but had not been a quick feature for Windows users until Windows 10.

Cortana was also included for this first time in Windows 10 (and was quickly disabled on my PC).

My favorite feature of Windows 10? Hard to say, but I think the most used feature is the ability to capture a screenshot and have it live in my clipboard. When it’s time to insert the screenshot, I simply CTRL+V it in or I use the hot key Win+V to have a menu pop up to browse all of my copied items and I can paste the item I wanted. I think I have used this feature 100 times in just this blog post!

Windows 11

A couple quotes from a recent Windows 11 preview and introduction:

“Modern. Fresh. Clean. Beautiful.” “We put ‘Start’ at the center. We put ‘You’ at the center.” … These technology drops are getting more and more emotional as the features change slightly…

Windows is releasing Windows 11….at some point. Some individuals have received the software, but I have yet to have access to the new operating system as of 10/25/2021. I always get a bit excited for change; I like adopting and testing new technologies. I am looking forward to some of the new changes, even including the new start menu. While I like the current version of the start menu, I do think there are ways to make the menu more intuitive with the room for added features. I want Windows to learn which apps I use when I open the start menu and place those first and easier to access.

More of the features can be found in this CNET Highlights video. I use the pen a lot with my Windows Surface Pro, so I am notably excited about the Haptics for the Windows Pen.


Windows 3.1


  1. Bryan Glick · ·

    Seeing these OS versions chronologically really puts the technological jumps Windows has made over the past few decades into perspective. Completely agree on how much of a swing and a miss Windows 8 was, in comparison to their other OS offerings. Granted, I think a lot of the modular risks they took with 8 to accommodate touch screens were necessary for the future of Windows OS, but boy was Windows 8 rough.

    Centering the menu with Windows 11 is an interesting move… I wonder if this is a move to stay more aligned with the strengths of the Mac OS UX, where keeping the focus to the center of the screen is so important. I am also surprised a lot of the UX found on phones (like suggestions of mostly used apps) haven’t found their way to full blown OS yet. Hopefully those sort of integrations start to make our laptop home screens feel just as advanced as our phone home screens.

  2. barrinja1 · ·

    Awesome blog idea, was fun to read through.
    In particular, was interesting during that absolutely electric ’95 launch that they introduced the “plug & play idea” – the first “platform” so to speak? It’s funny that Apple has gone on to be the King of harnessing the platform concept, when Microsoft beat them to the punch. Wonder if there’s been any studies on the leadership there and how they fumbled that…. same goes with the lead they had with Internet Explorer… had they had some of the Google vision on what that could be, wonder if they could have stayed on top.

  3. shanpopzaruba · ·

    Reading this and seeing the Windows 95 and Windows XP transported me back in time to the computer room in my childhood home — thanks for the blast of nostalgia. I appreciated your brief summary and critique of each! I used a PC all through college but transitioned to a Mac in grad school (around 2017), so I have not been around for the last few updates, but the saved copy features might change things — that seems so handy!

    All in all, really well written and brief but informative! Here’s to hoping you never have to think about Windows 8 ever again.

  4. lexgetdigital · ·

    Super cool blogpost, Brett! It’s impressive that you were able to chronologically review the updates, and that Windows digitally transformed each step of the way. I use a Mac for my personal computer (it was the only cool computer to have in middle school), but I’ve actually been questioning my choices lately (hopefully its not reading this and deciding to crash during exams….!). I use a PC for work and I actually really like the Start function. I guess I didn’t even realize how handy that was in comparison to no such option on my Mac (ugh, sorry old faithful).

    I’m curious about why you think they put the Start in the middle this time. Changes in operating systems tend to irritate users when they are drastic and/or different but unnecessary. Do you think that’s why you haven’t gotten the option for the 11? Too many complaints about people missing the Start option on the left? Hey, it’s been a thing since ’95!

    1. cloudbasedbrett · ·

      Great question…so I think Microsoft learned from Windows 8 and has made putting the start button back to normal a feature in W11.

      I think I’ll try it out in the middle and see if I like it better.

  5. Ah, good ol Windows 3.1

  6. Tanker 2 Banker · ·

    Windows 1 hurts my eyes just like a 90’s era Brunswick bowling scorecard interface. I was glad to see you didn’t skip over the shortcomings of ME and Vista. There are plenty of online debate rabbit holes as to which one was the worst. I find it interesting how opinionated and tribal people can be about their operating system of choice.

  7. Great post Brett! I really enjoyed learning the differences and features between each update of Windows throughout the years. Definitely have to agree that they really fumbled the bag with Windows 8. I remember specifically not updating my laptop to Windows 8, until I was absolutely forced to and glad they got rid of the forced tiles in the next update.

    Also fun fact: It’s estimated that the Windows XP default background ‘Bliss’ is the most seen photo in history!

  8. Brett- really cool idea for a blog post! I think the third week of class I shared on twitter a picture which showed the physical transformation of apple’s Macbook, which this post is a perfect compliment for (but for the wrong OS). One thing that I always was fascinated about is the early tech overlaps between the mac OS and then the launch of Windows OS (something early.. im forgetting the #). Obviously in a capitalist world, there is not need for collaboration and the tech share is illegal (unless bought.. which would also probably not be allowed under the anti-monopoly laws). BUT in my mind I crave a mac/windows tech share to create a best of both worlds computer. Alas.. I shall dream!

  9. Cool post Brett! Windows XP makes me nostalgic for when I used to open up my dads computer to use the paint application as a kid, thinking I was super cool and artistic. Computer softwares, be it Windows or Mac, have come a long way and it won’t be too long before we find the current versions out of date.

  10. greenmonsterbc · ·

    I love this post! Excellent deep dive into the history of window’s versioning and a solid review of the benefits each version brought forward. As the lead Release Manager for a large software company, I often find myself reviewing the various benefits an update/upgrade to more recent versions would have for both our clients and our company. Following semantic versioning ( the major release typically brings a re-architecture or significant change that may require your customer/client to change their behavior. These can backfire, depending on the amount of effort the client has to put in, but ultimately the benefits of modernization need to outweigh this pushback.

%d bloggers like this: