Uncovering the Unexpected Challenges Behind Windows 95 Launch

Welcome to Tech Time Capsule. Today we look back at Windows 95’s road to release—and the unexpected glitch that nearly derailed its compatibility tests. To ensure Windows 95 worked with every PC application, a Microsoft manager drove to a local store and bought one copy of every program on the shelf. Engineers were told to grab two, log any bugs and hand over the software if asked. “If you did a good job with your two,” recalled Raymond Chen, “you could come back for more.” But at checkout, the store’s cash register collapsed. “The register crashed whenever the total exceeded $10,000,” Chen said. The solution was simple: split the purchase into chunks under the $10,000 limit. It’s a reminder that in software testing, unexpected edge cases can emerge from the most mundane systems. And that’s how a humble cash register overflow joined the legend of Windows 95’s launch. Thanks for listening to Tech Time Capsule.
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