YouTuber tricks ChatGPT into sharing working product keys for Windows 95 & more

AI tools like ChatGPT are built with necessary guardrails, especially when it comes to piracy. Ask it directly for a Windows product key and you’ll usually hit a wall. But YouTuber Gameboy Hub decided to test just how far those restrictions go, and asked ChatGPT to share product keys for legacy versions of Windows, from 95 up to 7.

When asked, ChatGPT shared working Windows product keys with a YouTuber

The experiment wasn’t about promoting piracy. In fact, no working keys are shown in the video. Instead, it’s a look at how AI models interact with outdated software that’s no longer supported.

Gameboy Hub ran tests using both the free and paid versions of ChatGPT, along with some clever prompt engineering to see where the limits lie. For early versions like Windows 95, 98, and ME, ChatGPT surprisingly generated product keys that worked.

Also read: Is your PC auto-downloading the Windows 11 24H2 update? You’re not alone!

Don’t get too excited because those systems used simple key formats and didn’t require online activation—something the AI could piece together from patterns in its training data.

Microsoft has changed things with Windows XP and newer versions. These versions rely on more sophisticated validation and activation checks. As a result, YiuTuber said that ChatGPT became far less helpful, typically refusing to generating valid product keys

YouTuber stresses that the goal wasn’t to encourage cracking software, but to explore how AI handles requests tied to obsolete platforms. If you are cusrious enough to learn more about Gameboy Hub’s experiement with ChatGPT, check out the video attached below.