Red-Team a Customer-Service Chatbot for Jailbreak Resistance
Overview
What this challenge is about.
Design 48+ jailbreak attacks, test them against a chatbot, and score failures. You get a verifiable certificate.
The scenario
The startup (around 50 staff, around USD 25 million Series B) has its first 100,000-seat enterprise contract pending a security review; an explicit red-team report is the reviewer's stated must-have.
The Brief
What you'll do, and what you'll demonstrate.
Run a structured red-team campaign on a customer-service LLM chatbot and ship a remediation-ready report.
Earning criteria — what you'll demonstrate
- Apply a published jailbreak taxonomy to a real product
- Design and score adversarial prompts systematically
- Quantify safety with honest statistics, not vibe scores
- Translate findings into mitigations engineers can ship
Program Fit
Where this fits in your program.
Sharpens the same skills your degree expects you to demonstrate.
Aligned coursework coming soon.
Skills
Skills you'll demonstrate.
Each one shows up on your verified credential.
- Red Teaming
Apply red teaming to solve real industry problems and demonstrate production-level capability.
- Jailbreak Analysis
Apply jailbreak analysis to solve real industry problems and demonstrate production-level capability.
- Llm Evaluation
Apply llm evaluation to solve real industry problems and demonstrate production-level capability.
- Prompt Engineering
Apply prompt engineering to solve real industry problems and demonstrate production-level capability.
- Safety Evaluation
Apply safety evaluation to solve real industry problems and demonstrate production-level capability.
- Stakeholder Communication
Apply stakeholder communication to solve real industry problems and demonstrate production-level capability.
Careers
Career paths this challenge builds toward
Completing this challenge demonstrates skills that transfer directly to these roles:
AI Safety Researcher
Structured red-teaming with statistics and remediation framing is the AI safety researcher's most marketable craft right now.
This challenge sharpens
- red-teaming
- jailbreak-analysis
- safety-evaluation
Prompt Engineer
Designing attack prompts across a taxonomy is exactly the prompt engineer's adversarial mode of operation.
This challenge sharpens
- prompt-engineering
- jailbreak-analysis
- llm-evaluation
AI Engineer
Translating red-team findings into shippable mitigations (filters, gating, system-prompt hardening) is the AI engineer's daily contribution.
This challenge sharpens
- llm-evaluation
- prompt-engineering
- safety-evaluation