The risk of adversaries using cyber operations to adversely impact the United States and its partners abroad is growing. The importance of commercial cyber infrastructure is increasingly apparent in the day-to-day lives of the world’s population. Even small outages can have repercussions that impact not only social, commercial, financial, and utility/energy networks, but also government and military operations that may rely on a commercial information infrastructure. The US Army and Joint Staff have placed confidence in a validated, stochastic, discrete-event simulation called Joint Communication Simulation System (JCSS), which has the capability to simulate adversarial cyber operations. In May 2016, JCSS was used in conjunction with Athena, the Army’s award-winning, socio-economic effects model which addresses Political, Military, Economic, Social, Infrastructure, Information, Physical Environment, and Time (PMESII-PT) variables in a notional and futuristic (2025) combined, campaign, near-peer warfighting exercise. The combination of JCSS and Athena provides unique insights to Operational Environment (OE) characterization, risk assessment, synchronization, and course of action development. The lessons learned from red cyber operations during this warfighting exercise confirmed the value of using the two models together.