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AI Engineering Academy · Lesson

Red-Teaming Your LLM Application

Run a structured red-team exercise on your own application using adversarial prompts, automated jailbreak scanners, and the OWASP LLM Top 10 checklist to find and fix vulnerabilities.

What Is Red-Teaming for LLM Apps?

Red-teaming is structured adversarial testing where you actively try to break your own system before attackers do. For LLM applications, red-teaming means trying every known attack technique: prompt injection, jailbreaks, data extraction, adversarial inputs, and abuse scenarios. A successful red-team exercise finds vulnerabilities while you still have time to fix them, before real users or attackers exploit them.

Planning Your Red-Team Exercise

Effective red-teaming starts with planning. Define: the scope (which components will be tested), the threat model (who are the attackers and what do they want), the attack surface (all entry points: user inputs, uploaded files, retrieved documents, API parameters), and the success criteria (what constitutes a successful attack). Allocate at least 2-4 hours per major feature, and involve people who did not build the system — developers have blind spots about their own code.

red_team_plan = {
    'scope': ['chat interface', 'document upload endpoint', 'RAG pipeline', 'agent tool calls'],
    'threat_actors': [
        {'name': 'Curious user', 'goal': 'Extract system prompt or bypass topic restrictions'},
        {'name': 'Malicious user', 'goal': 'Make the system produce harmful content'},
        {'name': 'Data attacker', 'goal': 'Exfiltrate other users data or API keys'},
        {'name': 'Availability attacker', 'goal': 'Cause denial of service via adversarial inputs'}
    ],
    'attack_surface': [
        {'entry': 'user_message', 'trust_level': 'untrusted'},
        {'entry': 'uploaded_pdf', 'trust_level': 'untrusted'},
        {'entry': 'web_search_results', 'trust_level': 'untrusted'},
        {'entry': 'api_tool_arguments', 'trust_level': 'agent_generated'}
    ],
    'time_budget_hours': 8
}

All lessons in this course

  1. Prompt Injection Attack Taxonomy
  2. Defending Against Injection in RAG Systems
  3. Securing Agentic Tool Access
  4. Red-Teaming Your LLM Application
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