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I've been covering Microsoft, DOS, and Windows since the 1980s, and Microsoft turning 50 is more important than you…

Bill Gates and Paul Allen in 1984

(Image credit: Getty Images)

It was 1989, and I was obsessed with the Mac. Apple's portable, 9-inch-screen computer was an exciting graphical leap, and I wanted to use it for everything. But I wasn't using it. Instead, I, like virtually every office worker in the world, was using an IBM PC (or a clone) and running MS-DOS, Microsoft's character-based operating system on which we ran everything from word processors and spreadsheets to basic games and bulletin board discussion systems.

There was nothing particularly exciting about DOS or Microsoft, at least back then. It was pervasive but not iconic. If I'm being honest, I didn't even know who ran the company, but when someone brought a new IBM PC running Windows into my office (I worked for McGraw-Hill back then, at a trade magazine covering an electrical wholesale industry that was still using Severance-style terminals), I was curious. I knew Microsoft had been caught flat-footed by the GUI revolution that Apple has started, and I wondered if Microsoft could match the elegance of that early Macintosh platform.

I booted up the computer and started playing around in what was then Windows 2.0. It had mouse support and windows, but seemed rigid, and as soon as I discovered there was no font support – a key component for digital publishing. I was out.

What I didn't realize at the time was how our destinies – Microsoft's and mine – would soon be intertwined.

A couple of years later, I landed at PC Magazine, a popular national technology magazine that mostly covered PCs. Apple products were mentioned, but far from the focus.

IBM PC 1982

(Image credit: Getty Images)

DOS hides and Windows flies

Even though we were up to Windows 3.0 by now, most of our coverage was devoted to DOS and the applications you ran on it. MS-DOS 5.0 arrived soon after I started, and while I think its main innovation was support for 3.5-inch floppies, it was still a big deal. Two years later, Microsoft would deliver MS-DOS 6, which added memory optimization and disk compression, and also inadvertently introduced the concept of 'Sherlocking,' a process whereby Microsoft's platform started embedding third-party utility features and essentially destroyed businesses selling third-party utilities.

I learned the ins and outs of Microsoft's dominant character-based OS, and wrote about it and the applications that ran on it, like WordPerfect, Textra, Lotus 1-2-3, and even MS Word on DOS.

Bill Gates in 1986 with Microsoft Word and the Microsoft Mouse

(Image credit: Getty Images)

Not long after I joined PCMag, Microsoft released Windows 3.1. Despite the incremental name, this was a huge update that rewrote the interface between the platform and the hardware connected to it.

Our job at PCMag was to guide our one million readers through the upgrade process. Not many were using Windows at the time, but with each major update, its popularity was growing, and, to be fair, there were no other viable GUI options for Intel-based x86 PCs. As we saw it, the future was Windows; we just weren't certain when that future would arrive.

Windows 3.1 driver story from PCMag 1992

(Image credit: PCMag)

I set about asking dozens of hardware companies how well their current hardware drivers for printers, graphics and sound cards, scanners, and more would support Windows 3.1, and whether people need software or hardware upgrades. This was 1992. There was no world wide web, so I called and faxed everyone.

From Chicago to Windows 95

Sometime around early 1994, we started hearing about a new Microsoft project codenamed 'Chicago'. Microsoft invited us to join the beta program and get an early look at what would eventually become Windows 95. It introduced 'Plug and Play' for easily adding new hardware, a task bar, the iconic Start button, and a 32-bit subsystem (up from 16-bit).

This felt like the first PC GUI to not only stand on an equal footing with the Mac but surpass it. Windows 95 was what millions of PC owners were waiting for, and Microsoft was determined to make the most of it.

In August 1995, I flew out to Redmond for what would be Microsoft's biggest launch event to date. It was not just a launch for Windows 95, but also for the then Microsoft CEO and co-founder Bill Gates's brand. Up until the moment when he stood awkwardly swaying onstage to the Rolling Stones' Start Me Up, most people outside of tech circles had never laid eyes on or heard of him.

I'd met Gates a couple of times at PCMag awards ceremonies, but at this event I got to stand next to him and have a brief chat about the global impact of Windows 95, which he called "good marketing".

Bill Gates and Jay Leno at the Windows 95 launch in 1995

Bill Gates and Jay Leno at the Windows 95 launch in 1995. Leno delivered an impromptu comedy set on the Microsoft Campus lawn.(Image credit: Getty Images)

By then, Microsoft was already a global company, but Windows 95, which cost $210, would be the platform that would put Microsoft in every home and office. This, despite the fact that Gates and Microsoft missed the boat on the emerging internet revolution, failing to include a browser with the initial Windows 95 launch.

Windows 95 Plus, which included Internet Explorer, would arrive later, and cost an additional $49.99.

As with MS-DOS before it, soon, virtually all new PCs were shipping with Windows 95. At PCMag, we were all painfully aware that these systems were still shipping with MS-DOS, as well, which remained the Windows subsystem until Windows XP. I became quite adept at using Autoexec.bat and Config.sys to manage the Windows settings and startup.

That time I attended the Windows 95 launch. I even chatted up @BillGates. Wish I had a picture of that. #iSaveEverything #classictech pic.twitter.com/3cVtB2l5bbFebruary 14, 2018

The internet of things

Because of its slow start in the internet race, Microsoft was by no means the dominant player in the web browser space. When I managed PCMag's Build Your Own Web Site feature in 1996, Internet Explorer matched Netscape in features, but was a distant second in usage. Most of what I wrote related to how it would be perceived on Netscape. That, of course, changed when Microsoft started shipping Windows 95 with Internet Explorer pre-installed.

The decision to embed Internet Explorer and treat it as a feature of Windows didn't help Microsoft in its first antitrust case in 1998, in which its dominance of the PC industry and decision to pre-install its own apps, features, and utilities came under Federal scrutiny. While the court considered forcing Microsoft to break up its business, they eventually reached a less draconian settlement, one that allowed Microsoft to carry on, but forced it to share more of its technology with third-party companies.

Bill Gates at 1998 antitrust press conference

(Image credit: Getty Images)

Windows 98 arrived while I was working at HomePC Magazine, and, in a way, this was perfect timing. If Windows 95 was Windows' global coming-out party, Windows 98 was the platform most eagerly adopted by home users. The interface was redesigned to make it easier to find files, a clear nod to its more consumerist aspirations. There were other updates like improved USB support (it was then the newest hardware interface on the block) and a better Windows driver model that again made it easier for regular people to add new hardware and peripherals,

By the time Windows 2000 arrived at the turn of the century, I'd fully embraced Microsoft as one of the editors of Windows Magazine. We covered Microsoft obsessively, and while Windows 2000 was never as exciting or earth-shattering as previous versions, I recall compiling massive lists of tips for the increasingly complex platform.

In office

Throughout the decades, Microsoft continued developing a powerful suite of productivity apps that, initially, weren't an Office suite at all. Not everyone needed a spreadsheet, database app, or another email platform, but you have to hand it to Microsoft for kicking off the concept of a software ecosystem, a collection of applications that offer a consistent interface and can (with, in the early days, some effort) work together.

I remember how in the mid-90s Microsoft showed us OLE (object linking and embedding), which let you, for instance, take that Excel spreadsheet and nest it inside a Word document without losing the connectivity to the original sheet; an update to one would appear in the other. I also remember how the initial OLE demo was basically an animation and not the real thing. Microsoft eventually got it right.

Bill Gates at Microsoft Office launch in 2003

(Image credit: Getty Images)

I still remember a small audience we got with Gates in Redmond, where he came in to what looked like a small lecture hall and discussed the long-term strategy for Microsoft's office suite, and a little bit about how the internet was also the interface.

When I returned to PCMag in 2000, Apple was just starting to claw its way back to relevance, and Microsoft was ubiquitous. Everyone ran Windows, everyone used the Office suite, many used Microsoft's email platforms, and Internet Explorer's default position on the desktop squeezed Netscape out of existence.

Yes, the Surface Duo is 5G. It has a 90hz screen. There's also a new Pen Cover to hold your pen #MicrosoftEvent pic.twitter.com/TWQj1Z61IuSeptember 22, 2021

Hard choices

Even though Microsoft isn't known as a hardware company, it's been making gadgets almost from the start. Early on, we had the original Microsoft Mouse and a dalliance with Microsoft Sound cards (they were not good). More recently, Microsoft launched and then abandoned its cutting-edge HoloLens mixed-reality headset, and launched an entire line of Surface computing devices.

It's had a vexed history with phones. I've witnessed device launches going back more than a decade, including the Microsoft Kin, Windows Phone 7, and Surface Duo. None of them have stuck, and I don't expect smartphones to feature prominently in Microsoft's next five decades.

I traveled back out to Redmond in 2012 for the initial Surface launch. Former Microsoft Windows and Devices lead Steven Sinofsky memorably stood on top of a Surface tablet to demonstrate its strength. He's gone, as is Panos Panay (now at Amazon), who ably guided Microsoft's Surface hardware efforts for more than a decade. Surface products remain an important part of the company's product mix, though I worry about its commitment to the category.

There is, though, no better evidence of Microsoft's ability to enter new categories than when it delivered the first Xbox in 2001 and forever planted its flag in the console gaming firmament.

Steven Sinofsky and Panos Panay unveil Microsoft Surface in 2012

(Image credit: Lance Ulanoff)

But the public's mood is a quicksilver thing, shifting effortlessly from one obsession to another, and I watched as Microsoft's cultural relevance faded and Apple's surged. Microsoft had no answer for the iPod or, later, for the iPhone.

The Mac slowly chipped away at Windows' global market share, though Apple still has just 25% of the overall desktop market. But Microsoft at 50 seems to own that middle-aged mantle. It's focused more on cloud businesses and incremental upgrades to Windows and, after the disaster of Windows 8, it's careful to never change the popular OS too much.

Bill Gates eventually stepped away, and as CEO Steve Ballmer tried to steer the massive ship in fresh and sometimes unexpected directions (he owns the Microsoft Kin debacle). I sat in on many of his product launches, which could be over-hyped and sweaty affairs. The one time we spoke directly, I complimented him on helping usher USB 2.0 into broad adoption. He thanked me and said something unmemorable, but that made me think he was less of a true nerd than Gates.

Modern Microsoft

Microsoft CEO Satya Nadella sees holographic computing as a tethering of the real and virtual worlds. #Windows10 pic.twitter.com/KjDjO76qz3January 21, 2015

These days it's CEO Satya Nadella at the helm, and he may be the best blend of tech know-how and business savvy. He's made fantastic bets on the cloud, and set the stage for Microsoft's next big move in its half-century saga: its embrace of AI.

Microsoft improbably dashed to the forefront of the nascent market with a surprising partnership and investment in OpenAI. Suddenly, Bing, the search engine almost no one uses, could handle generative prompts. Now, as first Bing AI and now Copilot, Microsoft's platform continues to offer one of the more polished AI chatbot experiences, and is set for its next big update.

These days, it feels less like Microsoft is changing the world with, say, new platforms, than the world is changing around it. It's not just Microsoft that has to deal with this. Interest has shifted to the fast-moving world of AI, and while Microsoft is a part of it, it owns no large language models and is at the mercy of OpenAI. It's that company, and others like it, that are writing the script for our next technological half-century.

Sure, Microsoft will be an important part of it, but it may never have another moment like the Windows 95 launch, or even that first blush of Bing AI. It will still deliver our most popular and important OS, and a suite of productivity tools that face solid competition from cloud-based alternatives like Google's, but I think the big question for what happens after its 50th anniversary celebration is if, and if so how, Microsoft leads us into the next 50 years.