ChatGPT can now create Windows 95 activation keys — if you know what to ask

ChatGPT logo on phone sitting on laptop with OpenAI logo
(Image credit: Shutterstock)

ChatGPT can do a great many things, and it makes you wonder just what the limit of its capabilities actually are. Now one YouTuber has video evidence of the chatbot creating Windows 95 activation keys out of thin air. Which is perfect for any of those unlicensed copies of Windows 95 you still have lying around.

According to YouTuber Enderman, Windows 95’s validation mechanism is quite simple — which is why they chose it over more complex systems like Windows XP. However, ChatGPT is already designed not to facilitate piracy, and won’t generate a Windows 95 activation key if you ask directly. Not that this can stop you from getting a key out of the bot.

But because of how simple Windows 95 validation is, and the fact activation keys all followed the same basic format, Enderman’s new approach was to try and get ChatGPT to meet all the right criteria. That meant offering a detailed description of the Windows 95 activation key format, and attempting to get the bot to generate 30 facsimilies.

It took several attempts, and it seemed ChatGPT was having trouble understanding such strict and (apparently) complex criteria — particularly the parts that involved math. One of the numbers in a Windows 95 key needs to be divisible by 7, but unfortunately ChatGPT doesn’t appear to know what divisibility is — nor could it count the sum of its digits.

Speaking to Gizmodo, Enderman speculates that ChatGPT does know how to do math, but was getting lost during the batch generation phase.

ChatGPT has a lot to offer if you know what to ask

Eventually Enderman did manage to get ChatGPT to produce a result that included valid-looking activation keys. And upon testing one of those keys, Enderman was able to install Windows 95.

Enderman noted that GPT-3 was struggling to understand its constraints and would produce fewer usable keys as a result. Apparently tests with GPT-4 proved more fruitful, but the AI didn’t produce perfect results all the time. Unfortunately, it still took some doing.

When the YouTuber thanked the bot for providing free Windows 95 keys, it expressed confusion and reiterated that it’s unable to generate Windows 95 keys. Not that most people will have much use for an operating system that’s nearly three decades old. And, as Enderman noted, modern operating systems feature far more complicated validation processes.

But this goes to show that there are ways around ChatGPT’s blocks on specific kinds of content, and it’s not the first example we’ve seen. We already know how to get ChatGPT to answer any question, even if it has been banned, and a hacked “evil” version of the bot named Dan has no such content restrictions. ChatGPT has even been tricked into writing malware by some nefarious types.

Enderman’s workaround likely won’t stay available for long, and OpenAI is likely to patch up this exploit at some point in the near future. Not that the complicated series of instructions he offered can be considered a “workaround." 

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Tom Pritchard
UK Phones Editor

Tom is the Tom's Guide's UK Phones Editor, tackling the latest smartphone news and vocally expressing his opinions about upcoming features or changes. It's long way from his days as editor of Gizmodo UK, when pretty much everything was on the table. He’s usually found trying to squeeze another giant Lego set onto the shelf, draining very large cups of coffee, or complaining about how terrible his Smart TV is.