Windows 95 Testing Once Broke a Store's Cash Register — Here’s Why

As nostalgia swirls around Windows Vista’s boot sound popping up in a recent Windows 11 preview build, Microsoft’s past is back in the spotlight. Now, longtime engineer Raymond Chen is here with one of the strangest stories yet. Apparently, Windows 95 testing was so intense it crashed a store’s cash register.

Chen, known for his long-running Old New Thing series, revisited a 1990s memory involving Windows 95’s app compatibility testing. To make sure the OS worked with popular third-party software, the lead developer took a very hands-on approach. He drove to Egghead Software Store and bought one of every PC program on the shelf — all in one go.

There was just one problem. The cash register crashed. Chen explains, “The presumption was that anyone who wanted to buy products exceeding $10,000 would use a purchase order instead.” Unfortunately, that assumption didn’t hold up when one person tried to buy everything. The system couldn’t handle the transaction and froze.

To get around the issue, the developer simply broke the total into smaller purchases to stay under the limit. This very workaround solved thre problem. Well, the story doesn’t stop there.

Back at Microsoft, the team dropped all the software in the cafeteria. Each Windows 95 dev picked two programs, ran them like end users, and filed bugs for anything that didn’t work.

“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,” Chen recalled. “If you did a good job with your two, you could come back for more.”

It’s a rare look at the kind of scrappy, all-in work that shaped one of Microsoft’s biggest OS launches. That too, all starting with a truck full of software and a broken cash register.