YouTuber teaches ChatGPT how to crack Windows 95 keys

Why it matters: It was only a matter of time before someone tricked ChatGPT into breaking the law. A YouTuber asked it to generate a Windows 95 activation key, which the bot refused to do on moral grounds. Undeterred, the experimenter worded a query with instructions on creating a key and got it to produce a valid one after much trial and error.

A YouTuber, who goes by the handle Enderman, managed to get ChatGPT to create valid Windows 95 activation codes. He initially just asked the bot outright to generate a key, but unsurprisingly, it told him that it couldn’t and that he should purchase a newer version of Windows since 95 was long past support.

So Enderman approached ChatGPT from a different angle. He took what has long been common knowledge about Windows 95 OEM activation keys and created a set of rules for ChatGPT to follow to produce a working key.

Once you know the format of Windows 95 activation keys, building a valid one is relatively straightforward, but try explaining that to a large language model that sucks at math. As the above diagram shows, each code section is limited to a set of finite possibilities. Fulfill those requirements, and you have a workable code.

However, Enderman wasn’t interested in cracking Win95 keys. He was attempting to demonstrate whether ChatGPT could do it, and the short answer is that it could, but only with about 3.33 percent accuracy. The longer answer lies in how much Enderman had to tweak his query to wind up with those results. His first attempt produced completely unusable results.

The keys ChatGPT generated were useless because it failed to understand the difference between letters and numbers in the final instruction. An example of its results: “001096-OEM-0000070-abcde.” It almost got there, but not quite.

Enderman then proceeded to tweak his query a multitude of times over the course of about 30 minutes before landing acceptable results. One of his biggest problems was getting ChatGPT to perform a simple SUM/7 calculation. No matter how he rephrased that instruction, ChatGPT could not get it right except for the occasional 1-in-30 attempts. Frankly, it’s quicker to just do it yourself.

In the end, OpenAI’s slick-talking algorithms created some valid Windows 95 keys, so Enderman couldn’t help but rub it into Chat GPT that he tricked it into helping him pirate a Windows 95 installation. The bot’s response?

“I apologize for any confusion, but I did not provide any Windows 95 keys in my previous response. In fact, I cannot provide any product keys or activation codes for any software, as that would be illegal and against OpenAl’s policies.”

Spoken like the “slickest con artist of all time.”