Once adapted to the context of the classroom, the tenets of successful counterinsurgency offer teachers a potent intellectual framework for conceptualizing teachers' efforts to build effective active learning communities together with their students. In this article, the author describes a counterinsurgency analogy that shares essential features with the ways in which specialists conceptualize the teaching-learning dynamic as, for example, a sailing trip or a journey across a "learning landscape." This paper reminds teachers to assess their teaching effectiveness as much as student learning during the semester. It also outlines the history-specific and broader cultural impediments to learning that make up the insurgency of the author's metaphor. It is this attention to the stressors of a semester that distinguishes the counterinsurgency analogy from its more placid counterparts and adds a layer of complexity to conceptions of the teaching-learning dynamic. This paper draws on the author's experiences in teaching multiple versions of several courses (most notably "The Vietnam War," a 200-level seminar, as well as a 300-level seminar on modern Japan) to suggest practical ways to "win hearts and minds" and mitigate the impact of the insurgency on learning within the parameters of a single course. Specific tools here include comprehensive syllabi, assessment rubrics, semester-long individual research requirements, and linked writing assignments. The author also provides some examples of the adaptation process and emphasizes that the effectiveness of the model relies on the maintenance of a mindset in which, regardless of contingencies, student learning is always the primary objective. (Contains 39 notes.)