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This study investigates how school principals employ subversive strategies to question entrenched power structures and to transform policies, procedures, and practices that they believe are counterproductive. Specifically, the study examines what drives school leaders to be subversive, what the challenges and struggles are facing subversive leaders, and what strategies and tactics they use to navigate the educational system. Eighteen school principals from the Metro Vancouver Area were interviewed on their perceptions of subversive leadership. Four themes emerged: the rationale for being subversive, perceptions of subversiveness, the challenges and risks, and subversive strategies. The study provides some robust empirical evidence on how leaders seek to reposition their leadership strategies in opposition to the complacency of the status quo.