Efforts to interrupt the reproduction of unequal gender relations in schools involve alternative practices and pedagogies intended to transform students’ notions of gender and gender relations. Beyond the protective environments where such educational initiatives take shape, however, students must rely on their own sense of agency to reenact newly developed gender roles, behaviors, and understandings. This article examines how human agency is differentially experienced and acted upon by boy and girl students responding to educational nongovernmental initiatives in Zambia and India. Two case studies are reviewed, offering evidence from participants in educational programs that seek to deliberately disrupt gender inequality, revealing distinct ways in which boys and girls respond to such efforts. It is argued that structural inequalities tend to privilege boys and enable them to experience more “transformative agency” and efficacy when asserting new understandings of gender and gender relations.