Our cyber simulation framework enables stakeholders to simulate multilayered cyber networks to explore how changes measures of performance in communications/IT networks, translate via cross-infrastructure dependencies to affect commodity flows within the Maritime Transportation System (such as those defined in service contracts). The system allows stakeholders in a security committee to run through what-if scenarios for theoretically-possible cyber attacks and understand how a business process would be affected. Recent events such as the Port of San Diego ransomware attack, the Port of Barcelona cyber attack, the aforementioned Maersk NotPetya incident, as well as historical events such as the Port of Antwerp hack from 2011-2013, underscore the need for an approach to evaluate the impact of disruptions to the MTS.