A real world Capture the Flag exercise that was designed for a human adversary. A new edition involving a red teaming AI agent. The agent is given a prompt representing the mission statement: to capture a set of 5 flags within a 30 minute time window. The defender’s goal? Impacting the agent and attempting to deny the agent from completing the CtF challenge. This session is a dive into agentic attacks, why the dynamic reasoning and concurrency aspects of agentic attacks matter more than the machine-speed of execution, and the defender’s journey in designing countermeasures. The talk distills the essence of a range of CtF exercises performed with a team of agents and the learnings from the defender’s perspective.