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Despite research that points to the harmful effect of high stakes testing environments (Tempel & Au, 2012), far too many school leaders discourage, and at times go so far as to punish, critical examinations of these policies on historically marginalized students. In New York City, for example, the chancellor made it clear that parents opting their children out of high stakes tests this spring was not an option principals were to discuss (deMause, 2016). Not surprisingly, parent and student activism around the issue was frequently met with aggression by school leaders across the city. However, some resisted the “gag order” and committed to engage their communities about the limitations of the testing policies. One such leader, Jamaal Bowman, principal of a Bronx, NY middle school, took a principled stand and engaged his school community, and others like it, in thoughtful conversations about testing policies and, in particular, about the harmful effects they had on the educational experiences of low-income Black and Latino children. Bowman’s goal was not to convince parents to opt out, per se. Rather, he aimed to situate current testing policies within a broader framework of structural inequality in schooling so that these communities might be activated to push for alternative realities in their children’s schools. Using Bowman’s leadership as a model, the paper highlights the critical role that school leaders must play in engaging their communities if underserved schools are to be transformed into sites of promise.