Schools are beset with a serious “alienation gap” between teachers and students that is no less a problem than the “achievement gap.” Increasing student voice is thought to be one means to fill the gap, for it activates agency and thereby decreases passivity. The extent of agency ranges from attentive adult listening to strong student leadership. Here we concentrate on distinguishing elements of freedom, power, and authority in the enactment of agency, particularly how these elements can be distributed to students in urban authoritarian schools. In this article, four second-year Teach for America graduate students describe and reflect on their separate initiatives. Following the descriptions, the senior author, in a cross-case analysis, suggests factors associated with successful outcomes—enhanced self-esteem, individual rather than collective pride, careful consideration of the external context, constrained objectives, and the transfer of authority rather than power. We conclude that in troubled, impoverished schools, incremental change in distributing genuine authority is a promising possibility for enhancing school attachment.