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The current educational landscape for African American male adolescents operating within urban communities continues to pose both educational and socioemotional challenges. Education policies perpetuate failed promises far too often for African American male students in particular. Rather, their experiences manifest as academic disparities, mental health or adverse trauma or as disciplines that contribute to the school-to-prison pipeline (Ford & Moore, 2013). This article briefly explores the challenges Black boysface within urban school contexts and then espouses the strengths of African American youth. Next, the authors offer reimagined Broaching strategies (Day-Vines, et al., 2007; 2023) counselors can use based on Young et al’s (2017) leadership model when fostering culturally responsive services. In addition, group counseling leadership skills are reconceptualized as impacting students and entire school environments. Implications for counselor educators, practitioners, and policy makers are provided to advance the culturally responsive and courageous postures school counselors must embody to transform the urban schools and communities housing minority majority students and families.