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OSAI training (AI-300) - Advanced AI Red Teaming

OSAI training (AI-300) - Advanced AI Red Teaming

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Description

Organizations are increasingly using generative AI, machine learning, and autonomous AI agents. This leads to enormous innovation, but also to a rapidly growing attack surface that traditional security and pentesting methods are simply not designed for. The Advanced AI Red Teaming (AI-300) OSAI training is a unique, advanced AI cybersecurity training from OffSec (the organization behind, among others, OSCP) where you learn how to identify, investigate, and actively exploit vulnerabilities in these AI systems from an offensive perspective. 

With the rise of AI, not only technologies are changing, but also the risks. Models, data flows, vector databases, agents, and orchestration frameworks all bring their own vulnerabilities. And this is precisely where the focus of AI-300 lies: understanding how AI systems are truly attacked and how attackers think and act in such environments.

You will learn to adopt a true adversary mindset and combine it with proven offensive security techniques. You will specifically work with AI applications such as LLMs, deep learning models, and AI-driven infrastructures. How do you manipulate model behavior? How do you discover weaknesses in an AI pipeline? 

Advanced Red Teaming for AI Environments is a comprehensive, hands-on training where you learn how to actually attack modern AI systems. As organizations increasingly integrate LLMs, RAG pipelines, agents, and tool-calling frameworks into critical processes, it becomes essential to understand where these components fail and how they can be exploited. In this training, you will work with a structured and repeatable approach, based on frameworks such as MITRE ATLAS, the OWASP Top 10 for LLMs, and NVIDIA's AI Kill Chain. This way, you will learn step by step how to set up and execute complete AI attacks.

You will start by mapping the AI attack surface, analyzing model behavior, and conducting explorations on infrastructures where AI is integrated. Then you will get hands-on experience in practical labs. You will practice, among other things, prompt injection, manipulating RAG processes, data poisoning, influencing agents, abusing toolchains, and attacks on the supply chain. Attacks on protocols such as MCP and orchestration within multi-agent environments will also be covered. You will gradually develop the skills to identify vulnerabilities, simulate attacks, and analyze their impact within complete AI ecosystems. You will learn to approach AI systems as if you were an attacker, so you better understand where the real risks lie and how to help organizations defend against them.

Additionally, the emphasis is on stealth and OPSEC: how do you stay under the radar as an attacker? You will learn how to bypass AI-specific security measures and how attackers move from a compromised AI component towards broader enterprise environments. You will not only learn the theory but especially through practice. All topics are supported with realistic hands-on labs that simulate enterprise environments where AI systems are integrated with traditional IT and cloud infrastructures, allowing you to directly apply the techniques in professional red team scenarios. Think of scenarios with multi-agent systems, vector databases, and AI orchestration frameworks.

The training concludes with a capstone project, in which you perform a complete end-to-end AI attack on a realistic multi-agent enterprise environment. Here, you will bring together everything you have learned in one complete red team engagement.

Certification

Included in the training is the OffSec AI Red Teamer (OSAI) exam: an intensive 24-hour hands-on red teaming challenge where you must compromise a realistic AI-driven enterprise environment. If you pass, you will earn the OSAI and OSAI+ certification, demonstrating that you can professionally attack and assess AI systems. If necessary, a retake of the exam is also included within one year of receiving your materials.

Training Requirements

  • OSAI - AI-300 is bedoeld voor ervaren securityprofessionals die hun expertise willen uitbreiden richting AI-security en machine learning security. Denk aan Penetratietesters, Red teamers en Security Engineers.
  • De training is ook geschikt voor AI-engineers en developers die beter willen begrijpen hoe aanvallers AI-gedreven systemen aanvallen en die praktische technieken willen leren om AI-cybersecurityrisico’s te herkennen en te beperken.

Training Content

Je krijgt inzicht in hoe artificial intelligence-systemen het traditionele aanvalsoppervlak veranderen. Deze module introduceert de kernconcepten van AI-cybersecurity, legt uit hoe aanvallers AI-gedreven omgevingen benaderen en koppelt AI-aanvallen aan de red team lifecycle en moderne cyberdefensiestrategieën.

Je leert hoe je AI-applicaties, machine learning-componenten en modelinfrastructuur binnen een doelomgeving identificeert en in kaart brengt. Daarbij oefen je met reconnaissance-technieken om AI-assets, afhankelijkheden en blootgestelde services te ontdekken zonder de verdediging te alarmeren.

Je onderzoekt offensieve technieken om AI-agents te manipuleren via misbruik van prompt-instructies, geheugensystemen en tool-integraties. Deze module laat zien hoe autonome AI-toepassingen beïnvloed kunnen worden terwijl je onopgemerkt blijft.

Je analyseert de architectuur van multi-agent AI-systemen en leert hoe aanvallers vertrouwen tussen agents misbruiken. Je oefent met aanvallen zoals message manipulation, agent impersonation en workflow corruption.

Je bestudeert hoe retrieval-augmented generation (RAG)-systemen gecompromitteerd kunnen worden door knowledge sources te vergiftigen en retrieval-lagen te manipuleren om modeloutput te sturen.

Je leert de rol van embeddings binnen machine learning-systemen begrijpen en voert aanvallen uit zoals embedding inversion en informatie-extractie om gevoelige data uit AI-modellen te herleiden.

Je verkent hoe orchestratielagen en AI tool-integratieframeworks misbruikt kunnen worden om privileges te escaleren of ongewenste acties binnen AI-systemen uit te voeren.

Je leert hoe aanvallers de AI supply chain targeten, waaronder datasets, model weights, adapters en afhankelijkheden. Je oefent met technieken om kwaadaardige componenten in AI-omgevingen te introduceren vóór deployment.

Je identificeert kwetsbaarheden in AI-infrastructuur, waaronder cloud security platforms, modelservers en gecontaineriseerde machine learning workloads.

Je ontwikkelt strategieën om high-value AI-assets, trust boundaries en potentiële aanvalspaden in complexe AI-omgevingen te identificeren. Dit ondersteunt risicomanagement en versterkt threat detection-capabilities.

Je past alle technieken uit de training toe tijdens een volledige red team-opdracht tegen een realistische enterprise AI-omgeving, waarbij je simuleert hoe aanvallers productie-AI-systemen compromitteren.

Description

Organizations are increasingly using generative AI, machine learning, and autonomous AI agents. This leads to enormous innovation, but also to a rapidly growing attack surface that traditional security and pentesting methods are simply not designed for. The Advanced AI Red Teaming (AI-300) OSAI training is a unique, advanced AI cybersecurity training from OffSec (the organization behind, among others, OSCP) where you learn how to identify, investigate, and actively exploit vulnerabilities in these AI systems from an offensive perspective. 

With the rise of AI, not only technologies are changing, but also the risks. Models, data flows, vector databases, agents, and orchestration frameworks all bring their own vulnerabilities. And this is precisely where the focus of AI-300 lies: understanding how AI systems are truly attacked and how attackers think and act in such environments.

You will learn to adopt a true adversary mindset and combine it with proven offensive security techniques. You will specifically work with AI applications such as LLMs, deep learning models, and AI-driven infrastructures. How do you manipulate model behavior? How do you discover weaknesses in an AI pipeline? 

Advanced Red Teaming for AI Environments is a comprehensive, hands-on training where you learn how to actually attack modern AI systems. As organizations increasingly integrate LLMs, RAG pipelines, agents, and tool-calling frameworks into critical processes, it becomes essential to understand where these components fail and how they can be exploited. In this training, you will work with a structured and repeatable approach, based on frameworks such as MITRE ATLAS, the OWASP Top 10 for LLMs, and NVIDIA's AI Kill Chain. This way, you will learn step by step how to set up and execute complete AI attacks.

You will start by mapping the AI attack surface, analyzing model behavior, and conducting explorations on infrastructures where AI is integrated. Then you will get hands-on experience in practical labs. You will practice, among other things, prompt injection, manipulating RAG processes, data poisoning, influencing agents, abusing toolchains, and attacks on the supply chain. Attacks on protocols such as MCP and orchestration within multi-agent environments will also be covered. You will gradually develop the skills to identify vulnerabilities, simulate attacks, and analyze their impact within complete AI ecosystems. You will learn to approach AI systems as if you were an attacker, so you better understand where the real risks lie and how to help organizations defend against them.

Additionally, the emphasis is on stealth and OPSEC: how do you stay under the radar as an attacker? You will learn how to bypass AI-specific security measures and how attackers move from a compromised AI component towards broader enterprise environments. You will not only learn the theory but especially through practice. All topics are supported with realistic hands-on labs that simulate enterprise environments where AI systems are integrated with traditional IT and cloud infrastructures, allowing you to directly apply the techniques in professional red team scenarios. Think of scenarios with multi-agent systems, vector databases, and AI orchestration frameworks.

The training concludes with a capstone project, in which you perform a complete end-to-end AI attack on a realistic multi-agent enterprise environment. Here, you will bring together everything you have learned in one complete red team engagement.

Certification

Included in the training is the OffSec AI Red Teamer (OSAI) exam: an intensive 24-hour hands-on red teaming challenge where you must compromise a realistic AI-driven enterprise environment. If you pass, you will earn the OSAI and OSAI+ certification, demonstrating that you can professionally attack and assess AI systems. If necessary, a retake of the exam is also included within one year of receiving your materials.

Training Requirements

  • OSAI - AI-300 is bedoeld voor ervaren securityprofessionals die hun expertise willen uitbreiden richting AI-security en machine learning security. Denk aan Penetratietesters, Red teamers en Security Engineers.
  • De training is ook geschikt voor AI-engineers en developers die beter willen begrijpen hoe aanvallers AI-gedreven systemen aanvallen en die praktische technieken willen leren om AI-cybersecurityrisico’s te herkennen en te beperken.

Training Content

Je krijgt inzicht in hoe artificial intelligence-systemen het traditionele aanvalsoppervlak veranderen. Deze module introduceert de kernconcepten van AI-cybersecurity, legt uit hoe aanvallers AI-gedreven omgevingen benaderen en koppelt AI-aanvallen aan de red team lifecycle en moderne cyberdefensiestrategieën.

Je leert hoe je AI-applicaties, machine learning-componenten en modelinfrastructuur binnen een doelomgeving identificeert en in kaart brengt. Daarbij oefen je met reconnaissance-technieken om AI-assets, afhankelijkheden en blootgestelde services te ontdekken zonder de verdediging te alarmeren.

Je onderzoekt offensieve technieken om AI-agents te manipuleren via misbruik van prompt-instructies, geheugensystemen en tool-integraties. Deze module laat zien hoe autonome AI-toepassingen beïnvloed kunnen worden terwijl je onopgemerkt blijft.

Je analyseert de architectuur van multi-agent AI-systemen en leert hoe aanvallers vertrouwen tussen agents misbruiken. Je oefent met aanvallen zoals message manipulation, agent impersonation en workflow corruption.

Je bestudeert hoe retrieval-augmented generation (RAG)-systemen gecompromitteerd kunnen worden door knowledge sources te vergiftigen en retrieval-lagen te manipuleren om modeloutput te sturen.

Je leert de rol van embeddings binnen machine learning-systemen begrijpen en voert aanvallen uit zoals embedding inversion en informatie-extractie om gevoelige data uit AI-modellen te herleiden.

Je verkent hoe orchestratielagen en AI tool-integratieframeworks misbruikt kunnen worden om privileges te escaleren of ongewenste acties binnen AI-systemen uit te voeren.

Je leert hoe aanvallers de AI supply chain targeten, waaronder datasets, model weights, adapters en afhankelijkheden. Je oefent met technieken om kwaadaardige componenten in AI-omgevingen te introduceren vóór deployment.

Je identificeert kwetsbaarheden in AI-infrastructuur, waaronder cloud security platforms, modelservers en gecontaineriseerde machine learning workloads.

Je ontwikkelt strategieën om high-value AI-assets, trust boundaries en potentiële aanvalspaden in complexe AI-omgevingen te identificeren. Dit ondersteunt risicomanagement en versterkt threat detection-capabilities.

Je past alle technieken uit de training toe tijdens een volledige red team-opdracht tegen een realistische enterprise AI-omgeving, waarbij je simuleert hoe aanvallers productie-AI-systemen compromitteren.

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What Can I Learn After The OSAI training (AI-300) - Advanced AI Red Teaming?

  • A complete, structured methodology for applying AI red teaming, based on MITRE ATLAS, the OWASP Top 10 for LLMs, and NVIDIA's AI Kill Chain.
  • Mapping attack surfaces within modern AI systems, such as generative AI, LLM applications, and machine learning environments.
  • Performing embedding attacks and extracting sensitive information from AI models and machine learning systems.
  • Attacking AI infrastructure and deployment environments, including model servers, cloud platforms, and containerized workloads.
  • Perform advanced attacks such as prompt injection, RAG manipulation, data poisoning, exploiting agents and toolchains, and supply chain attacks.
  • Conducting explorations and modeling threats for AI-driven systems, including identifying trust boundaries and critical targets.
  • Exploiting weaknesses in AI orchestration layers and tool integration frameworks within modern AI applications.
  • Model extraction and performing adversarial machine learning attacks and manipulating AI systems.
  • Analyzing, compromising, and further penetrating complex AI environments, including multi-agent systems, tool-calling frameworks, orchestration layers, and AI-integrated cloud infrastructures.
  • RAG pipelines and vector databases are compromised through data poisoning and manipulation of the retrieval layer.
  • Identifying and exploiting vulnerabilities within the AI supply chain, such as datasets, models, and adapters.
  • Applying offensive methodologies to assess AI cybersecurity risks and strengthen risk management within AI environments.

Schedules

This training is scheduled as follows in the coming period. Missing a date? Feel free to contact us.

Date: 21 - 25 september 2026

Location: TSTC Veenendaal - Klassikaal

Date: In overleg te plannen

Location: TSTC Veenendaal - Klassikaal

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Frequently Asked Questions

AI-300 is an advanced AI cybersecurity training designed for participants with a solid foundation in cybersecurity. It is expected that you have experience with penetration testing, networking, Linux and Windows systems, and basic scripting. Basic knowledge of AI systems or machine learning, such as LLMs or generative AI applications, is a plus but not required. The focus is on offensive techniques to assess AI-driven systems, allowing participants without an AI background to successfully complete this training. OSCP or comparable practical experience is recommended.

Traditional penetration testing trainings focus on networks, web applications, and operating systems. AI-300 emphasizes the unique security risks posed by modern AI systems, such as generative AI applications, machine learning pipelines, AI agents, and model infrastructure. In this training, you will learn offensive techniques specifically developed to analyze and exploit vulnerabilities in these types of environments.

No, with the training you also receive a year-long access to OffSec's Learn One license, which includes all materials and labs associated with the training that must be completed before taking the exam. The 5-day classroom training provides a kickstart and helps you further if OffSec's 'try harder' motto does not meet your needs or fit you. During the training, you will go through a large number of challenging labs, and the theory is explained in more detail than in the self-study training. This way, you will better understand what you are doing in the lab environment even after the training, and you will receive assistance with individual questions or missing (prior) knowledge. Students from the classroom training pass faster, more often, and take the exam in many more cases than students who are fully reliant on the self-study training.

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