Understanding, anticipating, and identifying the wide array of evolving threats facing organizations today requires well-developed skills, experience, and analytical prowess. Table top exercises and expensive training courses can only get you so far. There is no better training method than creating real world quality adversarial sparring within the control of your own enterprise. Current Incident Response programs can integrate Red team exercises to simulate an adversary’s mindset and tactics, techniques, and procedures (TTPs) to mature processes, validate system protections and enhance the skills of staff. Adaptive red team exercises create a cycle of rapid improvement in both detection and response within today’s Blue Team programs. We will discuss real world examples to find deficiencies in staff skills, processes, and technologies. Along with the metrics and data to back it up.