Microsoft’s Windows 95 testing phase was so intense that it crashed cash registers with over $10,000 worth of software

We've taken a few trips down memory lane this week, even enjoying nostalgic treats from Microsoft itself. For example, Apple launched its "Liquid Glass" UI design as part of an iOS 26 overhaul at WWDC 2025, and Windows fans were quick to indicate that it was almost a bootleg version of Microsoft's Aero Glass from Windows Vista in 2006.

Then, Microsoft's iconic Windows Vista boot sound from 2006 made a surprise return in the latest preview builds of Windows 11. A "bug", they say.

Now, Microsoft veteran Raymond Chen has expanded on a comical tale about a time the company's application compatibility check for Windows 95 crashed a cash register at Egghead Software's store.

But to get the full gist of the story, we have to rewind even further to 2005, when Chen discussed Windows 95's development and the importance of the operating system's app compatibility in his Old New Thing series.

Interestingly, the engineer revealed that Windows 95's lead developer headed down to Egghead Software with his pickup truck to buy one copy of every single PC program in the store (via PCWorld).

The lead developer dropped the PC programs he'd bought at Egghead in Microsoft's cafeteria and asked every Windows 95 team member to pick two programs that they'd run application compatibility tests on.

According to Chen:

"The ground rules were that you had to install and run the program, use it like a normal end user, and file a bug against everything that doesn’t work right, even the minor stuff. (Of course, you had to provide the program to the person investigating the bug upon request.)"

"In exchange for taking responsibility for ensuring that Windows 95 was compatible with your adopted programs, you got to keep them after Windows 95 shipped. If you did a good job with your two, you could come back for more."

But perhaps more interestingly, the engineer recently revealed that the Windows 95 team lead's idea to check the operating system's app compatibility with a ton of PC programs almost didn't work.

He narrowed down the issue to a limitation that crashed the cash register at the Egghead Software store whenever a purchase exceeded $10,000. The presumption was that anyone who wanted to buy products exceeding $10,000 would use a purchase order instead.

However, the executive found a workaround for the setback, breaking his order into smaller chunks while ensuring that they didn't exceed the dollar limit. Problem solved.