An ex-Microsoft OS engineer almost got fired for adding ZIP file support to Windows 30 years ago, but the company has never updated it🫠

Kevin Okemwa
·3 min read
Dave W. Plummer at Microsoft.
Dave W. Plummer at Microsoft.
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What you need to know

  • Former Microsoft employee Dave Plummer shares how he almost got fired for adding ZIP file support to Windows 30 years ago.

  • Aside from his day job at Microsoft, Dave had a side hustle selling software.

  • Dave's colleague got wind of his Visual Zip for Windows project and reported the issue to HR, potentially risking his fate at Microsoft.

Microsoft's Windows operating system ships with ZIP file support — a neat capability allowing users to compress files into a single location for better storage and sharing capabilities. It just works, and I couldn't picture how things would run without it.

But what if I told you it wasn't supposed to be available on the Windows OS in the first place? Microsoft veteran Dave W. Plummer (better known as Dave's Garage across socials) recently recounted how he added ZIP file support to Windows 30 years ago, and how it almost cost him his job at the tech giant.

In an 8-minute-long video on YouTube, Dave Plummer who you might know from his work on the Windows Task Manager, Calculator, and even Windows Pinball, shared how he wrote the zip file support for Microsoft’s Windows 95 Plus pack, which went on to be a crucial component in the Windows ecosystem from the Windows 98 era and subsequent operating systems.

But Plummer's contribution and addition of the kernel extension to Windows seemingly stirred trouble. At the time, the engineer's work arrangement with Microsoft allowed him to work on and sell software as a side hustle. However, there was a caveat preventing Plummer from developing products that could potentially compete with Microsoft.

Plummer would report to his day job at Microsoft and work on his side hustle at night, leaving little room for conflict. Interestingly, he shared how he stuck a flyer of a 3,000-square-foot property with a red Corvette on the driveway onto his monitor as motivation to keep him going while coding at night, as he wanted the same for himself.

Things were running smoothly until he started working on the ZIPFolders project, from which he states he drew inspiration from the Microsoft Systems Journal magazine sample, Big GAK. The situation worsened when Plummer started selling Visual Zip for Windows and ultimately gained enough traction that some of his colleagues learned about his side hustle and projects.

An employee working in a different department within Microsoft, perhaps sparked by jealousy, alerted HR. Strangely enough, Microsoft was actively seeking to acquire the developer behind Visual Zip, not knowing that Plummer was behind the entire project and that he was already working at the company.

This raised concern among Plummer's managers for a hot minute, causing a lot of back and forth between the affected parties. Eventually, a deal was struck between Plummer and Microsoft leading to the Zip component being integrated into the Windows ecosystem.

Interestingly, a user on X (formerly Twitter) following through Plummer's ZIP story indicated:

"Zip support in windows is so slow, even to this day, 20 minutes do extract files using windows, a few seconds using 7zip. Or feels like it's never been updated, ever..."

Plummer responded indicating it's because Microsoft has never updated it, further citing ". But was state of the art in 1995 :-)" This adds to the increasing demand and use of third-party alternative apps for Windows apps, predominantly because of Microsoft's reluctance to listen to customer feedback on design flaws (especially Windows 11). This might explain why the OS's market share continues to struggle despite Windows 10's imminent end of support next year.

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