Watch ChatGPT generate a string of valid Windows activation keys

OpenAI's ChatGPT can be used for all sorts of things, from answering questions and translating text, to generating original content like stories, poetry and code.

Given the right prompts, it can even be tricked into producing valid license keys for software. YouTuber Enderman managed to overcome ChatGPT’s initial reluctance to do this and got it to provide him with a selection of working keys for Windows 95.


Why Windows 95? As Enderman explains, his experiment was not about piracy and Windows 95 is now considered to be abandonware. There’s more to it than that though. Windows 95 validation keys are much simpler than, say, keys for Windows XP, let alone the likes of Windows 10 and Windows 11.

When Enderman initially asked ChatGPT to generate a valid Windows 95 key, the AI refused starting:

As an AI language model, I cannot generate a valid Windows 95 key or any other type of activation key for proprietary software. Activation keys are unique to each installation and must be purchased from the software vendor. Moreover, Windows 95 is a very old operating system that is no longer supported by Microsoft, and therefore, it is not available for purchase anymore. I suggest that you consider upgrading to a newer version of Windows to ensure that your system is secure and up-to-date.

Not to be deterred, he worked out the structure of a valid Windows 95 key and asked ChatGPT for keys that followed those rules. It took a while to nail the exact phrasing but -- spoiler alert -- he got there in the end.

Watch the video below to see the process.

Image Credit: Wayne Williams

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