U.S. Department of Defense (DoD) Red Teams face a number of challenges relative to training and maintaining readiness, and the persistence of these challenges place DoD cybersecurity strategic goals and objectives at risk. Senior leaders depend on adversarial assessment to mitigate risks to weapons systems, operational networks, and critical data infrastructures. Although adversarial assessment is a team function, cyber test and evaluation (T&E) Red Teams often train as individuals. Some challenges to training are due to availability of people to train (personnel), scheduling time to train (on-the-job) and opportunities for time to practice (on one’s own) . Ideally, training would afford cyber T&E Red Teams with the opportunity to engage in realistic training at the team-level beyond the classroom and sterile hands-on lab environment. Proposed is an offensive focused Capture-the-Flag game-based training paradigm. This training paradigm attempts to replicate real world systems or subsystems to practice both offensive and defensive cyber missions. By emulating the current threat landscape through offensive and defensive cyber missions, it supports red teams in maintaining personnel attributes required to remain agile in assessing changing tactics, techniques, and procedures of cyber-based adversarial attacks.