SEC536: Adversarial AI - Penetration Testing AI Systems


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In 2026, many enterprise tenants are using AI agents that most identity teams have not yet tracked. Security operations centers are beginning to rely on AI help, but few organizations have set up proper oversight. Attackers are also changing their tactics. In just 18 months, the landscape has shifted, and most identity programs are still figuring out where to begin.
This 50-minute session is meant to give you an overview, not an in-depth analysis. The aim is to provide a clear map of where AI fits into your identity program, what the main components are, and which questions you should discuss with your team this quarter. We will cover three main topics, keeping each focused. First, we will look at the AI assets already in your tenant, such as Microsoft Entra Agent ID as a new type of identity, the Sponsor, Blueprint, and Runtime structure that every agent uses, and a brief overview of the OWASP LLM Top 10 and MITRE ATLAS taxonomies you should know. Second, we will discuss the defender's perspective, including what Microsoft Security Copilot does during an identity investigation and why you need to ensure reliable output before using Copilot in production triage. Third, we will talk about governance, including Microsoft's operational tools, Microsoft Agent 365 as the management platform for agents at scale, and the key regulations (NIST AI RMF, the EU AI Act, ISO/IEC 42001) your audit and risk teams will ask about. We will make sure to distinguish between Entra Agent ID (the identity object) and Agent 365 (the management product), since mixing them up is a common mistake.
We will briefly cover attacker-side AI with a few examples, rather than going into detail. The session will mention AI-assisted lure creation and the consent-grant attack pattern as it appears with AI plug-ins. More in-depth discussion of AiTM and consent abuse will be saved for the longer course.
By the end of the session, you should have a better understanding of the key components, the important products and frameworks to review, and a few questions to bring back to your own organization.
This session supports concepts from SEC559: Cloud and Hybrid Identity Security. To learn more, explore upcoming course runs, and access your free course preview, visit www.sans.org/sec559


Maxim Deweerdt is a Principal SANS Instructor and author of SEC559: Cloud and Hybrid Identity Security. With 15+ years in cyber defense, he brings deep expertise in identity-driven attacks, SOC operations, and detection engineering to every class.
Read more about Maxim Deweerdt