The transition from middle school to high school can be difficult for many students due to increases in school size, the structure of an academic schedule, and the complexity of social interactions in high school. However, Black boys face unique challenges during this transition period due to racism and structural inequalities. In response to these obstacles, schools across the country have created single-sex spaces specifically for Black boys to improve academic and social outcomes for students. The current study examines one such intervention located in an urban school district in the San Francisco Bay Area through interviews with four students to better understand how they make sense of their experiences within a specific single-sex classroom as they transitioned into high school. Findings from the study address the important role teachers play in shaping students' transitional experiences. Implications for single-sex learning spaces for Black boys are also discussed.