Christians seeking to nonviolently disrupt, engage, and transform structures of violence such as US militarism face a number of moral and political dilemmas. They must balance, on the one hand, their commitment to the faithful practice of religious life and, on the other, effective engagement in political change. When Christian theologians and ethicists have considered this relationship, they have tended to collapse the dialectic, privileging either effective engagement or faithful witness. When analysts of strategic nonviolence have taken it up, they have tended to neglect considerations of faithfulness, focusing largely on why nonviolence works. While each is instructive in its own way, these academic discourses have tended to ignore the actual contours of nonviolent actors’ deliberation as they engage the at times overlapping, complimentary, and competing demands of faithfulness and effectiveness. The aim of my dissertation is to offer a working account of practical reasoning that leaves in play both principles of faithfulness and effectiveness. I pursue this aim by executing an extended case study of the School of Americas Watch (SOA Watch), one of the longest running nonviolent social movements currently active in the US. I analyze four sites of practical reasoning—dilemmas related to liturgy, pluralism, law, and exemplarity—and in doing so theologically describe the ways in which SOA Watch activists deploy considerations of faithfulness and effectiveness as they discern how to engage politically. Rather than collapsing or evading the relationship between the two principles, these four dilemmas demonstrate a constellation of common forms in which nonviolent actors engage in the tasks of practical reasoning.