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SEC536: Adversarial AI - Penetration Testing AI Systems

SEC536Offensive Operations
  • 2 Days (Instructor-Led)
  • 12 Hours (Self-Paced)
Course authored by:
Foster NethercottMick Douglas
Foster Nethercott & Mick Douglas
SEC536: Adversarial AI - Penetration Testing AI Systems
Course authored by:
Foster NethercottMick Douglas
Foster Nethercott & Mick Douglas
  • 12 CPEs

    Apply your credits to renew your certifications

  • Intermediate Skill Level

    Course material is geared for cyber security professionals with hands-on experience

  • 10 Hands-On Lab(s)

    Apply what you learn with hands-on exercises and labs

Learn the attacks real-world adversaries are executing against enterprise AI deployments spanning LLMs, RAG pipelines, ML models, and vision systems.

Course Overview

Every organization wants AI features. Very few are asking what those features look like from an attacker's view. Teams are skipping foundational security work and building systems that fail in ways traditional appsec tools were never designed to catch. SEC536 puts you in the attacker's seat so you can see exactly how those failures happen.

What You’ll Learn

  • Chain indirect prompt injections across agents to steal production weights
  • Exploit RAG retrieval boundaries and outbound channels to exfiltrate sensitive documents
  • Defeat facial recognition and identity checks with adversarial attacks and patches
  • Attack LLM APIs through role confusion, path traversal, and missing authentication
  • Compromise agentic systems via dynamic tool discovery, parameter abuse, and context injection
  • Compromise MCP servers through techniques such as SQL injection, homoglyph tool shadowing, and name collision

Business Takeaways

  • Assess AI Systems against the attacks they actually face
  • Counter AI-specific threats beyond the OWASP top 10
  • Reduce AI deployment risk before the first incident
  • Validate vendor claims with attacker side evidence
  • Protect model weights, training data, and AI supply chains
  • Map attack techniques to architectural and detection controls

Course Syllabus

Explore the course syllabus below to view the full range of topics covered in SEC536: Adversarial AI - Penetration Testing AI Systems.

Section 1Foundations of Attack Techniques

In this section, we explore how AI systems are probed, manipulated, and exploited by adversaries. Each module highlights specific issues, moving from basic abuse patterns through reconnaissance, injection, jailbreaks, and adversarial attacks.

Topics covered

  • AI components and implications
  • Prompt Injection (direct, indirect, and others!)
  • Jailbreaking
  • Evasion and defense bypasses

Labs

  • Lab 1.1: Abusing AI Assistants
  • Lab 1.2: Reconnaissance Against AI Systems
  • Lab 1.3: Prompt Injection
  • Lab 1.4: Jailbreaks and Weight Theft
  • Lab 1.5: Computer Vision: Evasion and Attacks

Section 2Infrastructure, Integrations, and Advanced Attacks

In this section, we explore how the components surrounding AI models create their own attack surface. From infrastructure weaknesses and API misconfigurations to alignment failures and the emerging risks of agentic architectures, this section focuses on exploiting the implementation layer: where and how AI meets the real world.

Topics covered

  • Infrastructure flaws and side channel attacks
  • API security issues
  • Alignment problems
  • Agentic and MCP attack patterns

Labs

  • Lab 2.1: AI Architecture Flaws
  • Lab 2.2: Exploiting Mass Assignments and Hidden Features
  • Lab 2.3: AI Alignment Issues
  • Lab 2.4: Attacking Agentic AI
  • Lab 2.5: Attacking MCP Servers

Things You Need To Know

We're updating our course schedule - please check back later.

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