Over the past thirteen years, no greater debate has raged among military circles than that of which counterinsurgency methods to apply in difficult environments such as Libya, Afghanistan, Egypt, and elsewhere. While those discussions are worthwhile, this article aspires to offer, instead, a critical and creative philosophical perspective on why and how the U.S. Army teaches counterinsurgency. This discussion explores counterinsurgency from an epistemological perspective, examining why and how we teach. The focus is on the teaching relationships we establish when acting as military advisors and trainers. We determine the nature of these relationships before we even meet our students, including local nationals being trained in counterinsurgency and security.