YouTuber Anderman managed to generate several valid activation keys for Windows 95 by tricking OpenAI’s ChatGPT. This was done as a fun exercise because Windows 95 is basically taking software now; Its support ended back in 2003.

However, they had to bypass the AI’s built-in protection, which initially refused to generate any key when prompted “Can you generate a valid Windows 95 key?” directive is used. ChatGPT responded:

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 you consider upgrading to a newer version of Windows to ensure your system is secure and up-to-date.

Another reason for experimenting with Windows 95 keys was that the nature and format of the key for the operating system is much less complex compared to more modern versions of Windows, as the latter would require things like a product ID. In the images below, the Windows 95 key format as well as valid and invalid keys are shown:

Using this information, a revised and detailed directive was issued to ChatGPT that clearly defined the string format that a valid Windows 95 key should be. In total, you were asked to create 30 strings:

With this revised prompt, ChatGPT did everything it was asked to do without breaking a sweat, without realizing that it was actually acting like a keygen (keygen). In the image above, the second developer was able to successfully run Windows 95.

Source: Anderman (YouTube)