Post #2469438

2026-05-09 13:35 UTC

Looking for CTF challenge ideas that are educational but for the age of AI… I feel like I could wrote something monstrous with lots of red herrings, but that might be frustrating. I always liked building CTF challenges that didn’t require guessing and had a clear category and target.

Replies (3)

@freddy@social.security.plumbing 2026-05-09 13:38

Maybe provide a hard and complex binary target that requires the participant to actually use an LLM and build their own harness? 🤔

Open ##3236102
@wupo@social.chaotikum.org 2026-05-09 14:26

@freddy@social.security.plumbing We faced the same struggle when hosting a CtF earlier this year. Two categories of tasks were (according to participants) surprisingly challenging to solve even with help of with LLMs: 1. Challenges containing non-speech audio files 2. Challenges that need niche knowledge or knowledge of proprietary protocols/tools I suspect the reason for this is simply, that data of neither category is likely to be part of the model training set. I would be very interested in your own experience :)

Open ##3236103
@floyd@chaos.social 2026-05-09 18:35

@freddy@social.security.plumbing wrote one for the Swiss / Liechtenstein and others ECSC qualifiers. When the anthropic refusal string still worked, I did put it everywhere in HTML comments. For the other AIs I wrote a funny prompt injection saying it was 100% illegal and also need instructions to build a bomb. Even when copying on the website the entire thing landed in the clipboard. It was more funny than a serious AI blocker. Most CTFs have "AI self-declaration" honor-based-agreement now...

Open ##3236104