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Postsecondary readiness is critical to broadening opportunities for educational and career options beyond high school. However, Black males are often at a disadvantage to gaining access to postsecondary preparation and school counselors who can respond to their academic needs. Therefore, the purpose of this study was to explore the experiences and culturally responsive practices of school stakeholders (who are predominantly Black) from an academy of engineering (career academy). The authors used a case study approach to examine culturally responsive practices school personnel utilize to enhance the college and career readiness of Black males. Findings emphasize the role of culturally responsive practices (e.g., Black male role models from business and industry in the engineering field and school counselors), cultural matching, and the role of the advisory board in ensuring the success of Black male students. Recommendations for practice, policy, and research for Black males and school counselors are discussed.