This paper describes our ongoing efforts to improve current military wargame as used by the Dutch defence. In a typical wargame scenario military commanders and Intelligence officers are playing the game of blue and red forces, drawing their course of actions in order to outplay one and the other. Most of these games, as far as they don’t require fully scripted scenarios, are based upon regular, symmetric, and large scale military operations. These core models are usually based upon mutual attrition and require a lot of personnel. In this study, we focus on two particular issues. First of all, the configuration of a typical wargame scenario which is a complicated and time consuming process. Second, most wargames lack the incorporation of active non-combatants like civilians which are of utmost importance for the shape and dynamics of today’s battlefield. For both these issues we explore the usefulness of complex (adaptive) system knowledge and tools. Our aim is to use simple models of selforganization, both to simplify scenario configuration and to generate complex human behaviours. To do so, we study the use of various agent-based modelling approaches; in particular the well-known work of Axtell and Epstein on socio-cultural modelling called “Sugarscape”. We believe that, although these kinds of models are a very coarse and simplified representation of reality, they are useful in generating behavioural effects that mimic real-life patterns. Incorporating these models into a wargame context will confront military decision makers with the possible unforeseen higher order effects of their actions. Moreover, such an extended wargame would provide an interesting tool that could support evolutionary approaches to current military challenges