Microsoft’s Colorful History: The Legacy of 'Chicago' in Windows 95

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Ah, Microsoft! Its history is as colorful as a Windows 95 desktop wallpaper, complete with quirky codenames for everything from groundbreaking operating systems to behind-the-scenes projects. In a bizarre case of historical breadcrumbs, a recent report reminds us how these seemingly inconsequential codenames—like “Chicago” for Windows 95—can haunt us in unexpected ways, revealing the peculiar, deeply ingrained quirks of software development. Pour yourself a drink, grab a comfy chair, and let’s dive into some Microsoft nostalgia paired with a technical deep-dive you never knew you needed!

Chicago vs. Windows 95: What’s in a Name?

Let’s rewind the clock: the year was 1995. Grunge music was thriving, Toy Story was hitting theaters, and Microsoft was preparing to drop a bombshell in the form of Windows 95. This legendary OS, which introduced the world to the iconic Start Menu, had a colorful backstage pass known as “Chicago." But why this Windy City moniker, and why does it still pop its head up in unexpected places nearly three decades later?
According to Larry Osterman, a veteran Microsoft engineer, the codename “Chicago” became more than a placeholder. During Windows 95’s development, there wasn’t yet an official product name, and internal systems needed a way to differentiate it from other versions of Windows, particularly Windows NT. Thus, drivers intended for the future Windows 95 were labeled with the “$Chicago$” signature in .INF files—the configuration files that help hardware communicate with the OS. These files didn’t know the name Windows 95 yet, but they needed a distinct identity.
“But why not just update the codename later once you have the final name?” you might ask. Great question! Turns out, software engineers live by the adage, “If it ain’t broke, don’t fix it.” Updating driver signatures for a piece of hardware is costly and cumbersome—not exactly the sort of thing manufacturers are eager to tackle unless absolutely necessary. And so, the “$Chicago$” signature stuck around. It did its job quietly, even as the world moved on to Windows XP, Vista, 7, and beyond. Who knew this little remnant of the ’90s would still lurk quietly in configuration files, like an Easter egg in Microsoft’s OS history?

The Technical Side of $Chicago$: What Exactly Are INF Files?

For the uninitiated, .INF files are configuration files used by Windows operating systems to install software and drivers. Imagine them as detailed instruction manuals that explain how to handle a piece of hardware (like your network adapter or printer). These files list essential information, including supported OS versions. In Windows 95’s case, the “[Signature]” section could include entries like $Windows NT$ or $Chicago$.
This system was a sort of handshake between the operating system and the driver. However, when Windows 95 was still under development, those writing drivers couldn’t just say, “Windows 95,” because it didn’t technically exist yet! Enter: $Chicago$.

Codenames Can’t Keep a Secret: The Risks

The enduring existence of codenames doesn’t just amuse software historians—it can also lead to misunderstandings and even missteps in engineering. Take, for instance, Osterman’s commentary on how such tags could reveal sensitive project details inadvertently. “Codenames sometimes leak,” he warns—quite literally in some cases, serving as breadcrumbs that curious minds can follow back to yet-to-be-disclosed details.
Here’s an example of a codename gone rogue: Turbine. A Microsoft staffer once used this codename for a Windows Server Azure Edition project. Somewhere along the way, it cropped up in an SDK, where developers mistook it for an unreleased Xbox project. The rumor mill spun wildly until clarification arrived.

Why Do Codenames Persist? Functionality Meets Nostalgia

Microsoft isn’t alone in its codename culture. Whether it’s Apple’s “Bordeaux” or Google’s dessert-inspired Android names, developers love these playful tags. But unlike Apple’s or Google’s more public-facing strategy, Microsoft’s codenames often linger in the background, rarely meant for external use. Yet engineering quirks—like the reluctance to change a proven driver signature—can lead to long-term persistence.
Sound strange? It’s not just poor project management or laziness. Updating systems post-production (especially for something as sensitive as hardware drivers) can introduce errors—those dreaded bugs—and make hardware behave unpredictably. Imagine hundreds of manufacturers each scrambling to update their driver configurations, only to face millions of frustrated users when things stop working.

Windows 95 and the NT Divide: A Kernel of Truth

It’s worth noting that when Windows 95 hit the scene, Microsoft maintained two distinct OS paths: Windows 9x for consumers (using the “Chicago” kernel) and Windows NT for enterprise use (with the “NT” kernel). These paths merged later, but during that time, separate driver infrastructures were required. With no synergy between the NT and 9x worlds, differentiating these systems wasn’t just optional—it was necessary.
Osterman also pointed out that after Windows XP, the kernel divide disappeared. But even so, the old signatures like $Chicago$ remained. Why? Because, again, why risk breaking compatibility? For manufacturers, the stakes were high, and mindlessly doing away with historical codename tags made no business sense.

The Broader Implications: Why Does This Matter?

So, what does this teach us—beyond feeding our nostalgia and trivia appetites? Here’s what we can take away:
  1. Backward Compatibility Matters
    Microsoft—and the tech industry at large—carries a responsibility to maintain compatibility across decades of devices and configurations. Whipping out a shiny new OS doesn’t mean breaking everything that came before it.
  2. Cost vs. Risk in Engineering
    Technical debt isn’t just some abstract concept; decisions made years ago live on because the cost of change—whether monetary or reputational—outweighs any potential benefit.
  3. Codenames in Software and Beyond
    Codenames aren’t just placeholders. They reflect the human side of development, showcasing engineers’ creativity, humor, and occasional folly. Yet, as stories like Turbine have shown, they may also hint at the risks of poor communication or unintended leaks.

In Conclusion: The Spirit of $Chicago$ Lives On

The story of Microsoft’s “Chicago” codename isn’t just a nostalgic trip down memory lane. It’s a lesson in the complexities of product development, the weight of legacy systems, and the quirky cultural artifacts that emerge from years of iterative innovation. As we boot up our modern Windows 11 systems, let’s take a moment to appreciate that somewhere, in some small corner of a .INF file, $Chicago$ might still be waving at us, a quiet witness to the old battles of OS development.
So, next time your PC boots up without a hitch, tip your hat to the forgotten codenames, the unsung drivers, and the engineers who keep it all humming along. Now, who’s ready to install Windows 95 just to relive the teal-hued nostalgia? Just kidding—leave that relic in the past... probably.

Source: The Register When old Microsoft codenames crop up in curious places
 


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