The process of translating socio-cultural understanding and models into improved military effectiveness and expanded capabilities often seems sisyphean in its difficulty. This paper describes the clash of cultures that occurs when the deterministic mindset meets non-deterministic models and in which the desire for prediction can only be met by descriptive models. This disjuncture is exacerbated by the fact that the vocabularies, modeling assumptions and data sets that have supported the military modeling and simulation community do not provide adequate bases for the inclusion of social science models. We contend that in such an environment, solutions must be crafted to be specific to missions, areas of operation (geographic regions), levels of command (tactical, strategic, etc.) and operator skill level. By using the above parameters to clarify needs, the community will be better positioned to provide viable solutions supported by available data that can meet the expectations of end users.