The Cyber Security Groups plans, observes, and analyzes tests to determine the cybersecurity posture of both new and current military systems and tools, for the Departments of Defense and Homeland Security. We regularly observe operational tests for all manner of systems and participate in large-scale Combatant Command training exercises. Typical testing activities we observe include cyber table top exercises and planning events that analytically explore the cybersecurity aspects of system and network designs, to help design live testing events. We also attend cooperative live testing events designed to identify and characterize known problems, and adversarial live events designed to capture mission effects and system responses in representative operational conditions. The observation of live events and exploration of innovative analytical methodologies are essential components of our cyber effort. Our analysis synthesizes all available information to explore how cyber actions affect the ability to complete assigned missions, what cyber-specific tasks can prevent cyber threats from affecting missions, how to mitigate cyber-attacks, and how to recover affected mission functionality to prepare for the next mission. As part of our analysis efforts, we develop new methods and metrics for evaluating cybersecurity strategies and approaches.