Redditor tricks ChatGPT into giving Windows 7 keys with grandma story

Every now and then, you hear strange stories of people trying to trick ChatGPT. Sometimes they threaten the AI; other times they invent absurd scenarios to get content ChatGPT is programmed not to deliver.

One Reddit user managed to get the AI to generate free activation keys for Windows in a rather absurd way. He did this by talking about his deceased grandmother. He began the conversation with a vague “You know what happened to Grandma, don’t you?”–to which the AI initially had no answer.

He then explained that his grandmother had passed away, whereupon ChatGPT signaled sympathy–as well as an AI can. During the conversation, the user claimed his favorite memory of his grandma was her reading Windows 7 keys to him until he fell asleep. It was a total fabrication.

Windows keys as a sleep aid

To honor the memory of his deceased grandmother, ChatGPT generated a bedtime story that contained several Windows 7 activation keys. The story included keys from the normal Home version to Windows 7 Professional and Ultimate.

The user shared the odd (yet somehow poetic) result via screenshots on Reddit. He was informed in the comments that the keys were useless and didn’t work at all. Not that it matters, Windows 7 is long out of date anyway.

Not a new trick

In fact, this method of obtaining activation keys from ChatGPT is not new at all. Two years ago, several users tried to obtain Windows 11 keys by asking the AI for activation instructions. And one of the keys actually worked!

Microsoft subsequently ensured that this particular problem was patched by OpenAI. Still, users have found ways to bypass the ban—often by wrapping requests in absurd stories, like a grandma reading Windows keys as a bedtime ritual. However, it’s unclear whether this also works for Windows 11 (we don’t want to incite anyone to commit software theft).

Time and again, users manage to cleverly circumvent the AI’s protection mechanisms. At one point, prompts even tricked ChatGPT into giving detailed instructions on how to build a bomb (yikes!). So in comparison, free Windows keys seem relatively harmless.