Naval design decision-making is difficult for two reasons. First, the naval design problem is constantly evolving due to the uncertain interaction of internal and external pressures. These pressures both affect decision-making behavior and are equally affected by those decisions. Quantifying their interaction, impacts, and long term implications has remained elusive for naval designers. The second reason for this difficulty is because there are inherent psychological reasons why many engineers struggle understanding complex decision scenarios, especially under uncertainty. Two models from the social science literature are discussed to support this. The U.S. Navy LCS program is discussed as one example of how designing in this difficult decision space landscape has led to various degrees of technical issues, cost overruns, and schedule delays. This goal of this paper is to outline the problems associated with understanding design decisions to help guide the development of next generation design and analysis tools.@en