Skip to main content
  1. Home
  2. Computing
  3. News

Someone just used ChatGPT to generate free Windows keys

ChatGPT is an incredibly capable piece of tech, with a huge number of interesting uses. But, perhaps inevitably, people have put it to use for less noble purposes. Now, someone has used it to generate valid Windows license keys for free.

The discovery was made by YouTuber Enderman, who used ChatGPT to create license keys for Windows 95. Why Windows 95? Well, support ended for it 20 years ago, so this was essentially an exercise in curiosity from Enderman rather than an attempt to crack more modern versions like Windows 11.

Activating Windows with ChatGPT

As well as that, Windows 95 uses a simpler key validation method than later versions of Microsoft’s operating system, meaning the likelihood of success was much higher.

Recommended Videos

Ordinarily, ChatGPT will reject attempts at piracy. We tried asking it to “generate a valid Windows 11 key,” only for ChatGPT to respond: “I’m sorry, but generating a valid Windows 11 license key would be illegal and unethical. It is also not possible for me to do so as I am an AI language model and do not have access to such information.”

Surprisingly easy to do

A MacBook Pro on a desk with ChatGPT's website showing on its display.
Hatice Baran / Unsplash

Still, fooling ChatGPT into generating the keys appears to have been pretty straightforward for Enderman. Once they knew the format Windows 95 uses to generate keys, they simply asked ChatGPT to give them a set of text and number strings that matched the rules used in Windows 95 keys. That required some basic math, but not much else.

Because this request was not an obvious attempt to create a registration key and do something illegal, ChatGPT had no problem complying. After a few refinements to the request from Enderman, the chatbot was able to provide 30 sets of registration keys for Windows 95, of which at least a handful were valid. Interestingly, the only thing stopping ChatGPT from creating a greater number of usable keys was its faulty math ability.

While this application of ChatGPT is sure to raise a few eyebrows, it would be much harder to pull off for more recent Windows versions given the increased complexity of their keys. Still, it’s an indication of just what ChatGPT can do if you get a bit creative with your prompts. From writing malware to composing music, people have been keeping OpenAI’s chatbot busy, and we wouldn’t be surprised if more key-generation attempts come to light after this latest escapade.

Alex Blake
Alex Blake has been working with Digital Trends since 2019, where he spends most of his time writing about Mac computers…
I tested over a dozen laptops in 2025, and these are my top picks for Black Friday
Need something that's not a MacBook? These two Asus laptops offering something better.
On the tabletop, there's an Asus ROG Zephyrus G14 laptop

A reliable laptop is one of the best investments you can make. And if you’ve been searching across websites and e-commerce pages looking for the best deals on laptops, I've got you covered with two of my favorite picks. 

Asus ZenBook A14 (45% off)

Read more
Intel might return to Apple laptops, but not the way you think
A new report suggests Intel could act as a foundry for Apple’s M-series chips, but not a full return to x86.
Intel Xeon wafer.

What’s happened? While Apple and Intel had cut ties a long while ago, things might look different in the near future. A fresh leak from Ming-Chi Kuo suggests that Intel may return to the Apple world. Not as the CPU designer, but as a chip foundry for Apple’s lower-end M-series silicon. This isn’t a throwback to Intel-powered MacBooks; instead, Intel would simply manufacture chips that Apple designs. In fact, if things go right, Intel could start supplying these chips by mid-2027.

The plan involves using Intel’s 18AP process node to fabricate Apple’s entry-level M-series chips (likely for MacBook Air/base iPads).

Read more
Windows 11’s “fast” File Explorer is slower than ever and hogs more RAM
The background-preload trick fails to beat Windows 10’s Explorer performance, proving some old habits die hard.
Computer, Electronics, Laptop

What’s happened? Microsoft rolled out a background-preloading update for File Explorer in Windows 11 Insider builds, hoping to make it open faster and feel smoother. The idea here was to keep parts of Explorer loaded in memory, so it pops up instantly when you click it. While that sounds smart, the reality is quite the opposite. As revealed in testing by Windows Latest, Explorer still lags compared to Windows 10, and preloading ends up using more system RAM.

In side-by-side tests, Windows 11’s “preloaded” File Explorer opened slower than Windows 10’s regular Explorer, even on lightweight hardware.

Read more