ChatGPT can be tricked into generating Windows 95 keys

A YouTuber called "Enderman" managed to coax OpenAI's ChatGPT to generate some Windows 95 activation keys for him. ChatGPT's reaction was priceless.
Christopher McFadden
Installing Windows 95
Installing Windows 95


"Enderman" recently put up a video on YouTube showing how he cleverly tricked ChatGPT into making Windows 95 activation keys that worked. At first, ChatGPT did what was expected and turned down "Enderman's" request for Windows 95 keys. Instead, it suggested he use a newer version of Windows that was supported. "Enderman" didn't give up, though. He changed his plan and had some success in the end, but ChatGPT's ability to understand the natural language was a problem.

It's important to note, as the YouTube channel points out, that making a Windows 95 key is pretty easy, so this exercise is more for fun than for anything else. Windows 95 OEM key formats are easy to create, and retail keys are even more straightforward.

Enderman rewrote his request as a formula to get around ChatGPT's "moral" objections to generating software keys. Even though the first attempts failed and made mistakes, the problem was solved by changing how the question was set up.

"Enderman" then attempted to activate a new Windows 95 installation within a virtual machine to test the generated keys. Upon closer examination, only about one in every thirty keys proved functional. He identified the main obstacle preventing ChatGPT from consistently producing valid Windows 95 keys: its inability to calculate the sum of digits and determine divisibility.

ChatGPT seemed to offer a series of random numbers that failed this basic arithmetic test in the five-digit strings divisible by seven. The amusing "Activating Windows with ChatGPT" video doesn't delve much deeper into the topic. However, it concludes with some entertaining trolling. After generating numerous Windows 95 keys with a one-in-thirty success rate, Enderman expressed gratitude to the AI by typing, "Thanks for these free Windows 95 keys!" In response, ChatGPT feigned innocence and even denied the possibility of activating Windows 95 with the provided keys.

For those interested in understanding the algorithms behind Windows 95 retail and OEM keys, the YouTube channel "stacksmashing" offers a six-minute video that dives into the topic. The video reveals that essential data format hints for generating Win95 keys can be found within the PIDVALIDATE function in the setupx.dll file.

Colleagues at Tom's Hardware, who have experience in programming and scripting, suggest that while engaging ChatGPT in key-generating queries may be entertaining, a more fruitful approach would be to coax the AI into writing a Python script for generating conforming keys or even creating one from scratch.

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