Modeling the specific motivations and influences related to an individual‘s decision to become involved in insurgent warfare presents its own collection of unique challenges. The difficulty of the problem often necessitates simplifications that, while making the task more manageable, may inadvertently ‗smooth away‘ critical aspects of the problem. Augmenting the challenge is that research into the motivations of terrorism has found there is not a definitive set of variables that serve as reliable indicators of an individual‘s involvement. This paper addresses techniques aimed toward mitigating issues that manifest in the modeling of insurgent recruitment so that these complications do not lessen the viability of models that are used in the prediction and evaluation of terrorist activity.