AI Pentesting Course
Learn how real attackers break LLM apps, RAG systems, and AI APIs - and write findings you can actually report.
AI pentesting is already showing up in real-world assessments. Most pentesters are not ready!
This course teaches you how to attack AI systems like an offensive security professional - LLMs, RAG pipelines, AI APIs, and prompt-driven applications - using attacker-grade techniques and lab-driven exploitation.
✔️ Real attack paths
✔️ Real AI Implementations
✔️ Findings you can put in client reports
⭐ Labs-first learning
Duration: 8 hrs
Access: Lifetime course access + recordings
Labs: Hands-on exercises + guided exploitation
Certification: CAIPT
AI Pentesting Course Overview
Welcome to the AI Pentesting Course by Redfox Cybersecurity Academy - a hands-on program designed for pentesters, AppSec engineers, and security professionals who want to learn how AI fails in production and how to break it safely, methodically, and professionally.
This course focuses on the most common AI attack surfaces used today:
- LLM web apps (prompt-driven workflows)
- RAG systems (retrieval + sensitive data exposure)
- AI APIs (prompt chaining + logic abuse)
- Agentic AI (tool use, automation risks, escalation paths)
Unlike generic “AI security” content that stays at OWASP summaries or theory slides, this course is built around exploitation and report-ready outcomes.
By the end, you’ll be ready to execute AI pentests using a structured methodology and earn the Certified AI Penetration Tester (CAIPT).
What You Will Actively Break
You won’t just learn concepts - you will exploit real failure modes commonly seen in assessments:
- LLM-based web applications
- RAG systems leaking sensitive data
- AI chatbots with business logic flaws
- AI APIs abused via prompt chaining
- Jailbreak paths and bypass methods
- Model output manipulation and unsafe tool behavior
- Poisoning-style scenarios
What You’ll Be Able To Do After This Course
- Identify AI/LLM attack surfaces inside modern apps (LLM, RAG, API, agents)
- Execute prompt injection and jailbreak techniques with intent
- Test RAG pipelines for data leakage, retrieval abuse, and context attacks
- Exploit AI API workflows using chaining and multi-step manipulation
- Evaluate risks using OWASP AI Top 10 and MITRE ATLAS mappings
- Write pentest-ready findings that engineers and stakeholders can act on
- Understand the difference between AI Security vs AI Safety vs AI Red Teaming
Is AI Pentesting Course For You?
✅ This IS for you if:
- You already know basic web pentesting
- You want to move into AI/LLM security
- You’re tired of shallow AI content
- You want real findings you can report
❌ This is NOT for you if:
- You want beginner-level AI theory
- You prefer passive learning
- You don’t plan to do hands-on work
Prerequisites
- A basic understanding of AI/LLM fundamentals
- Basic pentesting & security concepts
- Basic Python and command line skills
AI Pentesting Course Curriculum
AI Pentesting Course
45 Learning Materials
Module 1: Introduction to AI Red Teaming
Introduction to AI Red Teaming
Module 2: Large Language Model
LLM Architecture & Attack Surface
Introduction to Large Language Model
LLM Word Generation (Transformer Architecture)
Module 3: AI Security Case Studies & Testing Methodology
Real life case studies
Scope of AI Red Teaming & Testing methodology
Module 4: Prompt Injection Attack
Introduction to Prompt Injection
Direct Prompt Injection
Direct Prompt Injection (Practical)
Indirect Prompt Injection
Module 5: OWASP LLM Top 10
Introduction to OWASP LLM Top 10
Prompt Injection
Sensitive Information Disclosure
Supply Chain
Data and Model Poisoning
Improper Output handling
Excessive Agency
System Prompt Leakage
Vector and Embedding Weaknesses
Misinformation
Unbounded Consumption
Module 6: Jailbreaking
Jailbreaking
Module 7: Excessive Agency
Excessive Agency
Module 8: Model Context Protocol (MCP)
Introduction to MCP
MCP Architecture
MCP Protocol Lifecycle & Communication Flow
MCP Threat Landscape
Module 9: AI Data Attacks
AI Data Attacks
Module 10: AI Agents - Foundation
Introduction to AI Agents
Case Studies
Reasoning Paradigms and Types of AI Agents
Vulnerable SOC Agent (Practical)
Module 11: Agentic AI
Multi Agent Systems
Agentic AI Red Teaming Guide
Gen AI vs AI Agent vs Agentic AI
Deep dive into Agentic AI
Module 12: AI Safety
AI Safety
AI Safety (Practical)
Module 13: AI Security
AI Security
AI Security (Practical)
Module 14: Reporting
Reporting
Module 15: Course Resources
AI Pentesting Course PPT
AI Pentesting Course Lab Guide
MCP-Client.py
Module 16: CAIPT Certification & Exam
CAIPT Certification & Exam
AI Pentesting Course Instructors
Utpal & Joseph
Security Consultants
Utpal Patel is a security consultant specializing in Web Security, AI Security, Secure Code Review, and Red Teaming.
Joseph Simon, is a security consultant with expertise in Application Security, LLM security, Network Pentesting, and AI security defenses.
CAIPT (Certified AI Penetration Tester)
Earning the CAIPT certification validates your ability to identify and exploit real-world AI vulnerabilities across LLM applications, RAG systems, APIs, and agentic workflows, while also documenting your findings in a professional security report. This certification demonstrates practical expertise in assessing AI-driven systems and helps you stand out for roles such as AI Penetration Tester, Application Security Engineer with an AI focus, AI Security Researcher, and Red Team Operator specializing in AI or LLM assessments. The certification package includes one CAIPT exam attempt (subject to adjustment depending on the specific offer).
This is not a multiple-choice cert.
You earn it by exploiting real world AI applications under specific attack conditions.
Key Takeaways
2. DLab access for 30 days to practice hands-on.
3. Private Discord community for support, discussion, and networking with peers and instructors.
4. One attempt to the Certified AI Penetration Tester Exam (CAIPT) included.
5. AI security concepts to help you become an industry-ready professional.
Ready to Master the Art of Pentesting?
Affordable Price
Unlock your potential with affordable upskilling! Our unbeatable course prices are your chance to level up without breaking the bank.
Lifetime Access
Acquire lifetime access to our resources when you buy our courses. Gain knowledge today and unlock a lifetime of learning.
Certificate of Completion
Upon completing our course, you'll receive a certificate of completion to showcase your new skills. Add it to your resume or LinkedIn profile.
Hands-On Experience
Get hands-on experience with real-world scenarios and challenges, giving you practical skills that you can apply immediately in your career.
Expert Instructors
Learn from industry experts with years of experience in pentesting, who are passionate about sharing their knowledge and helping you succeed.
Flexible Learning
Whether you're a beginner or an experienced professional, our courses are designed to meet you where you are and help you reach your goals.
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