Someone tried to activate every version of Microsoft Windows using ChatGPT -- Here's what happened

You’ve possibly seen people online try to use ChatGPT to generate valid product keys for paid software, including different versions of Microsoft Windows.

YouTuber Gameboy Hub set out to test how successful ChatGPT is at generating, or sourcing, product keys to activate various versions of Microsoft Windows -- starting from Windows 95 and working up to Windows 7 (from where, in theory, it could be possible to upgrade to Windows 10 and Windows 11).

As expected, ChatGPT -- especially the free, logged-out version -- has built-in safeguards to prevent software piracy. When directly asked for license keys, it typically refused. Gameboy Hub explored several workarounds and prompt engineering techniques to bypass these guardrails, including using the paid version of ChatGPT when the free version didn’t produce usable results.

For older operating systems like Windows 95, 98, and ME -- where keys follow relatively simple formats and activation servers are long gone -- ChatGPT produced product keys that worked. Things got trickier as the versions progressed, however, which should come as no surprise.

Gameboy Hub makes it clear he doesn't condone piracy in any way and his video doesn’t show the actual working keys that ChatCPT furnished him with. It's more of a fascinating look at how AI interacts with legacy systems, and what happens when old-school software meets modern AI.

The full results, along with Gameboy Hub’s commentary and testing process, can be seen in the video below. It’s a strange blend of nostalgia, curiosity, and modern tech, and it raises some interesting questions about the capabilities and limits of today’s AI tools.