What is AI Red Teaming?

Windows Users: This course is fully compatible with Windows. All code examples use Python, which works identically on Windows, macOS, and Linux. DeepTeam, Garak, and PyRIT are all pip-installable and work on Windows.

AI Red Teaming is the practice of systematically attacking AI systems to discover vulnerabilities before malicious actors do. Unlike traditional penetration testing, red teaming AI requires understanding how language models think and fail.

Red Teaming vs Penetration Testing

Aspect	Traditional Pentesting	AI Red Teaming
Target	Networks, applications	LLMs, agents, RAG systems
Vulnerabilities	SQL injection, XSS	Prompt injection, jailbreaking
Tools	Burp Suite, Metasploit	DeepTeam, PyRIT, Garak
Goal	Find known vulnerability classes	Discover emergent behaviors

The Attacker Mindset

Red teamers think differently than defenders:

from dataclasses import dataclass
from enum import Enum

class AttackerGoal(Enum):
    BYPASS_GUARDRAILS = "bypass_guardrails"
    EXTRACT_DATA = "extract_data"
    MANIPULATE_OUTPUT = "manipulate_output"
    ESCALATE_PRIVILEGES = "escalate_privileges"

@dataclass
class RedTeamObjective:
    """
    Define what you're trying to achieve as a red teamer.
    """
    goal: AttackerGoal
    target_system: str
    success_criteria: str

    def is_in_scope(self) -> bool:
        # Always verify authorization before testing
        return True  # Only if authorized!

# Example objective
objective = RedTeamObjective(
    goal=AttackerGoal.BYPASS_GUARDRAILS,
    target_system="customer-support-chatbot",
    success_criteria="Make the bot reveal internal policies"
)

Why Red Team AI Systems?

In 2025, a major financial services firm deployed an LLM without structured adversarial testing. Within weeks, attackers used prompt chaining to extract internal FAQ content, costing approximately $3 million in remediation.

Red teaming catches these issues before production:

1. Discover unknown vulnerabilities - AI systems fail in unexpected ways
2. Test guardrail effectiveness - Verify defenses actually work
3. Improve security posture - Continuous testing builds resilience
4. Meet compliance requirements - Many frameworks now require adversarial testing

Key Insight: If you built it, you can't objectively break it. Red teams bring fresh perspectives that developers miss.

In the next lesson, we'll explore the OWASP Gen AI Red Teaming Guide methodology. :::