Microsoft Engineer Tells Anecdote about Windows 95: Orders More than $10,000 Cashier System Crashed

Passionategeekz On June 18, Microsoft’s senior engineer Raymond Chen shared a short story from 30 years ago on the Microsoft Developer Blog last week.

He shared a small story on August 24, 2005, which is a follow-up to that story.

Simply put, Microsoft once sent a Windows 95 development manager to drive to a local software store (Egghead Software) to purchase, and the development manager bought all the PC programs in the store (one for each program).

I’ve told the story of a Windows 95 development manager buying all PC programs in the Egghead Software store.

Later I learned that in addition to surprise the store manager, this idea almost failed: when the total price exceeds $10,000, the store cashier system will crash.

The reason is simple – who would buy a product worth $10,000 as soon as he entered the store? This kind of bulk purchase should use purchase orders, right?

The final order was split into multiple batches to ensure that the total amount of each batch does not exceed US$10,000 (Passionategeekz Note: the current exchange rate is approximately RMB 71,877).

In 2005, he also shared another case of Windows 95 crashing the cash register.

The St. Louis Post reported that the local CompUSA store found its cash register system collapsed at midnight, causing customers to be forced to stand for 90 minutes. Similarly, the root cause of the failure is a vulnerability in the cashier software – the vulnerability has not been discovered since the store was never open until midnight.

In addition, there is also a joke about Windows 95 being released in Hong Kong that was written as “Mindows 95”. Apple also took the opportunity to take advantage of the popularity and launched a marketing advertisement related to it (it took too long and could no longer be tested).

According to Microsoft, Raymond has been involved in the development of Windows systems for more than 30 years. He occasionally appears on Windows development blogs or official X accounts to share some interesting development anecdotes with users.

In 2003, he also founded a website called The Old New Thing, which was much more popular than expected. It is said that this situation will still make him feel uncomfortable even today. The website later gave birth to a book, which coincidentally also titled “Old Things and New Talks” (released by Addison Wesley Press in 2007).

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