Stability and Support Operations (SASO) are becoming increasingly important in modern military operations. Conflicts are no longer comprised solely of two opposing sides engaged in combat on an open battlefield. Instead, they are more likely to involve groups sharing various alliances and relationships each pursuing a range of different goals. The Sheherazade SASO wargaming engine presented here: a) incorporates subjective criteria for scoring Course of Action (COA) success such as the animosity between factions and attitudes of locales, b) uses non-traditional units such as refugees, media and information operators, and c) employs a co-evolutionary genetic algorithm in modeling the dynamics of the complex multi-sided simulation for generating COAs. This paper outlines our approach towards the development of a wargaming model that handles the more complex and computationally demanding arena of SASO.