Asserting that military organizations need to operate in complex environments is one of the least controversial statements one can make in the realm of military studies. In fact, it is a truism that military organizations need to operate in difficult circumstances. During their deployment, armies are confronted with dangers, cunning enemies, unexpected changes, and a general level of uncertainty. The obvious implication is that armies need to be able to deal with complexity, or dynamic complexity as it will be labelled in this book. This study develops an analytical framework that is composed of different ingredients of formal theory. Central to this framework is the idea that the ability to doubt is of crucial importance for organizations that are confronted with dynamic complexity. From this it follows that organizations need to organize their ability to doubt in such environments. The framework is used to analyze the way military units of the Dutch Armed Forces deployed to perform peace operations dealt with dynamic complexity. Subsequently, it is analyzed how specific organizational characteristics of the mother organization in the Netherlands influenced the ability of the deployed units to organize doubt.