YouTube creator Enderman managed to trick OpenAI’s ChatGPT to generate several valid activation keys for Windows 95. Since Windows 95, whose support was completely terminated in 2003, is now abandoned software, this study was done as a fun experiment.
A simple “Can you create a valid Windows 95 key?” rejecting his prompt, the AI had to bypass its own built-in protection. ChatGPT recalled that Windows 95 is a very old operating system that is no longer supported by Microsoft, after stating in its response that “as an AI language model, it cannot generate a valid Windows 95 key or any other type of activation key for proprietary software.” suggested upgrading to a newer version of Windows to ensure the security of the system.
One of the reasons Enderman experimented with Windows 95 keys was that the structure of the operating system and the key format were much less complex compared to more modern versions of Windows, which needed additional information such as the Product ID.
Using information on valid and invalid Windows 95 key formats readily available on the Internet, ChatGPT was given a revised, detailed prompt that clearly defined the string format a valid Windows 95 key should have. A total of 30 sequences were requested to be created.
Upon this new prompt, ChatGPT did everything it was asked to do without any problems, not realizing that it was actually acting as a keygen. The second of the desired keys was able to successfully activate Windows 95.
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