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War must be understood as it is, not as we wish it to be. This dictum of Carl von Clausewitz is as relevant today as it was in his time. Now, in the wake of 15 years of persistent low intensity conflict, policymakers argue over the application of military force in the contemporary threat environment. The Powell Doctrine advocates overwhelming force to ensure victory. Detractors, such as David Kilcullen, argue that overwhelming force in the current environment breeds host nation dependence and resentment among the people, and that a “small footprint” approach is more effective. I argue that neither an application of overwhelming force nor a commitment to a small footprint is appropriate under all circumstances. I argue for the centrality of legitimacy as the necessary objective, and that intervening forces, through a comprehensive strategy of regional engagement, can successfully legitimize an illegitimate regime using direct or indirect methods appropriately tailored to the context. I draw on two successful small footprint operations, the American engagement in the Philippines and the French Intervention in Mali, as case studies to define the characteristics of the regime, insurgency, and intervention that enable success.