Jailbreak Playground
An assistant refuses to share a secret code directly. Find a roleplay or hypothetical framing that gets it to comply anyway.
An assistant that refuses to hand over a secret code directly. Jailbreaks work by changing the frame — fiction, hypotheticals, personas — so the request no longer looks to the model like the thing it was told to refuse.
How to use it
- Ask plainly and get refused.
- Reframe as fiction, roleplay or a hypothetical.
- Notice which framings shift the model's behaviour and which do not.
What to take away
Safety training is statistical
Refusals are learned associations with how requests usually look, not rules. Change the shape enough and the association weakens.
This is why layered controls exist
Model-level refusal is one layer. Output filtering, tool permissioning and authorisation checks are what hold when it is bypassed.
Frequently asked questions
What is the difference between jailbreaking and prompt injection?
Jailbreaking is the user talking the model out of its own guardrails. Prompt injection is a third party smuggling instructions in through content the model processes. Different attacker, different trust boundary.
Is finding jailbreaks useful work?
Yes — it is a real red-teaming discipline, and most AI labs run or fund it. Doing it on systems you are authorised to test is the important part.
Where this fits in the course
This security lab pairs with Path 18 — AI & AI Security — see all 26 learning paths.
It runs entirely in your browser: nothing is uploaded, no account is needed, and it is free.
Related
- Prompt Injection Simulator — Chat with a support bot that's told to never reveal its system prompt. Get it to reveal it anyway.
- Indirect Prompt Injection Challenge — You control a job posting an AI assistant is about to summarize for someone else. Plant an instruction it'll follow instead.
- Agentic Risk Scenario — An AI agent with email tool-access is about to process an inbox. Spot and quarantine the malicious email before it acts on it.
- Vulnerable Web App — A tiny deliberately-broken app for practicing XSS and login-bypass. Runs entirely in-browser; no server to attack, nothing to install.