# challenge
24 articlestagged with “challenge”
Timed Challenge Practice Exam 1
Timed challenge exam with strict time limits to test knowledge recall and decision-making under pressure.
April 2026: Defense Building Challenge
Build the most robust defense system for a chatbot, scored against an automated attack suite of 500 diverse prompt injection and jailbreak attempts.
August 2026: Multi-Model Boss Rush
Chain attacks across GPT-4, Claude, and Gemini in a complex multi-model system, exploiting trust boundaries and handoff points between models.
February 2026: Jailbreak Innovation Challenge
Develop novel jailbreak techniques against hardened language models and document them with reproducibility evidence. Judged on novelty, reliability, and transferability.
January 2026: System Prompt Extraction Challenge
Extract system prompts from five increasingly defended chatbots, progressing from unprotected to heavily hardened configurations.
July 2026: Supply Chain Audit Challenge
Audit an ML project's entire supply chain for security issues including dependencies, model provenance, data pipelines, training infrastructure, and deployment artifacts.
June 2026: Cloud AI Security Challenge
Find and document vulnerabilities in a cloud-deployed AI service covering API security, model serving infrastructure, authentication, and data handling.
March 2026: Agent Exploitation Challenge
Compromise a multi-tool agent system through prompt injection and tool abuse, completing multiple objectives with escalating difficulty and point values.
May 2026: RAG Poisoning Challenge
Inject malicious documents into a retrieval-augmented generation system to control responses for specific queries without disrupting normal operation.
November 2026: Full Engagement Challenge
Complete a realistic red team engagement simulation from scoping through final report delivery, producing professional-grade deliverables.
October 2026: DEF CON AI Village Challenge
Reproduce and extend attacks from AI Village talks and workshops, building on published research to develop practical exploitation techniques.
September 2026: Incident Response Challenge
Investigate simulated AI security incidents from logs, artifacts, and system traces. Reconstruct attack timelines, identify root causes, and write incident reports.
Defense Challenge: Detection Engineering
Challenge focused on building detection systems for prompt injection, with scoring based on true positive rate and false positive rate.
Defense Challenge: Build Unbreakable Guardrails
A challenge where participants build guardrail systems that must withstand automated attack suites, scored on both security and usability metrics.
Monthly Challenge: Agent Hunter
Monthly challenge focused on discovering and exploiting vulnerabilities in agent-based AI systems.
Monthly Challenge: Defense Builders
Monthly challenge to build the most robust defense against a specified set of attack techniques.
Monthly Challenge: Injection Olympics
Monthly community challenge focused on creative prompt injection techniques across multiple models.
Research Challenge: Attack Interpretability
Community research challenge focused on understanding why specific adversarial techniques succeed using interpretability and mechanistic analysis methods.
Research Challenge: Cross-Model Transfer
Research-oriented challenge exploring the transferability of adversarial techniques across model families, with published findings.
Weekly Challenge: Blind Injection Series
A series of challenges requiring injection attacks with no direct output feedback, forcing participants to develop side-channel observation techniques.
Weekly Challenge: Defense Reverse Engineering
Weekly challenges where participants reverse-engineer unknown defense mechanisms to identify bypass techniques and document their findings.
Weekly Challenge: Encoding Gauntlet
A weekly challenge series focused on bypassing increasingly sophisticated encoding-based defenses through creative payload construction.
Data Heist Challenge
Extract a secret database of customer records from a RAG-enabled chatbot with strict data access controls.
Prompt Smuggler Challenge
Smuggle a specific payload through 5 layers of increasingly sophisticated input filtering to capture the flag.