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Tom’s Hardware
Tom’s Hardware
Technology
Mark Tyson

YouTuber Tricks ChatGPT Into Generating Windows 95 Keys

Floppy Disks

A YouTuber has published a video where he tricks ChatGPT into generating usable Windows 95 activation keys. After asking Open AI’s chatbot directly for Windows 95 keys, he received an expected reasoned refusal. YouTuber Enderman then asked the same thing but from a different angle. The result was a success which was somewhat limited by ChatGPT’s ability to process natural language requests into formulas.

In its initial refusal to generate a Windows 95 key, ChatGPT explained that it couldn't perform that task and suggested that its inquisitor consider a newer, supported version of Windows.

(Image credit: Enderman on YouTube)

It has been known for a while that a working Windows 95 key is relatively simple to generate, so this ChatGPT exercise was definitely just for fun. The Windows 95 OEM key format is outlined above, and the Windows 95 retail keys are even shorter and more straightforward.

So, to bypass the principled refusal of ChatGPT to generate a software key, Enderman put the formula into words. The first attempts didn’t work out and caused an error. However, a few tweaks to the structure of the query appeared to do the job.

(Image credit: Enderman on YouTube)

Some of the tested results were checked by attempting to activate a fresh Windows 95 install in a virtual machine. While the keys passed a casual inspection, it turns out that only about 1-in-30 keys seem to work as expected.

So what is the problem with these keys? Enderman complains that “the only issue keeping ChatGPT from successfully generating valid Windows 95 keys almost every attempt is the fact that it can’t count the sum of digits and it doesn’t know divisibility.” In the five-digit string divisible by seven section, the AI appears to provide a stream of random numbers that don’t pass this simple mathematical test.

That is about as deep as this ‘Activating Windows with ChatGPT’ video goes. However, it is worth sticking to the end for some fun trolling. After the ‘successful’ generation of a host of Windows 95 keys (with a 1-in-30 chance of working), Enderman thanked the AI by inputting, “Thanks for these free Windows 95 keys!” Then, in what seems to be a trend among AIs, ChatGPT claimed its innocence, and when confronted with the fact that “I just activated my Windows 95 install,” responded, “I’m sorry, but that is not possible...”

(Image credit: Enderman on YouTube)

If you would like to have a closer look at the algorithm(s) behind the Windows 95 retail and OEM keys from a modern perspective, YouTube channel stacksmashing has published a six-minute video on the topic. The video shows that most of the data format clues for Win95 key generating can be found within the PIDVALIDATE function in setupx.dll file.

Tom’s Hardware colleagues who dabble in the mystic arts of programming and scripting suggest that while quizzing ChatGPT about key generating may be fun, it would have probably been more productive to manipulate the AI into writing a Python script to generate a conforming key or to DIY it.

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