A YouTuber recently posted a video in which he successfully tricked ChatGPT into generating usable activation keys for Windows 95. Initially, he asked OpenAI’s chatbot directly for the keys but received a predictable and logical refusal.
YouTuber Enderman attempted the same request but from a different angle. This time, he was successful, although ChatGPT’s ability to process natural language requests into formulas was limited.
ChatGPT initially declined the request to generate a Windows 95 key, citing its inability to perform the task and suggesting that the requester consider a more recent and supported version of Windows.
Although generating a working Windows 95 key is relatively simple, this exercise with ChatGPT was done purely for entertainment purposes. The Windows 95 OEM key format is outlined above, and the retail keys are even shorter and easier to understand.
Enderman managed to bypass ChatGPT‘s principled refusal to generate a software key by putting the formula into words. Although the first attempts resulted in an error, a few tweaks to the query structure eventually did the job.
Some results were used to activate a fresh Windows 95 install in a virtual machine to test the generated keys. While the keys appeared to pass a casual inspection, it was discovered that only about few-in-30 keys actually worked as expected.
So, what was causing the problem with these keys? Enderman explained that “the only issue preventing ChatGPT from generating valid Windows 95 keys almost every time is its inability to count the sum of digits and determine divisibility.” In the section with the five-digit string divisible by seven, the AI seemed to provide a random stream of numbers that did not meet this simple mathematical requirement.
The “Activating Windows with ChatGPT” video concludes shortly after demonstrating the successful generation of a handful of Windows 95 keys, despite their limited functionality. Enderman thanked the AI for the keys by inputting, “Thanks for these free Windows 95 keys!” However, as is common among AIs, ChatGPT claimed its innocence when confronted with the fact that the keys had been used to activate a Windows 95 installation, responding with, “I’m sorry, but that is not possible…”
For those interested in a more detailed look at the algorithms behind the Windows 95 retail and OEM keys, the YouTube channel stacksmashing has published a six-minute video on the topic.
The video reveals that most of the data format clues for generating Win95 keys can be found within the PIDVALIDATE function in the setupx.dll file.