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Transitioning from middle to high school involves several challenges for students, including attending a new school, meeting new teachers, the introduction of a rigorous curriculum, and navigating an unfamiliar learning environment. These environmental shifts coupled with poor school attendance, behavioral infractions, and low course grades drastically lower ninth-grade retention rates especially for African American males. An on-time promotion to the tenth grade is a critical predictor of an on-time high school graduation. The purpose of this qualitative, exploratory single-case study was to explore the perceptions and experiences of African American males who attended a ninth-grade academy and had an on-time promotion to the tenth grade. Five themes emerged after conducting semi-structured interviews and reviewing students’ archival data.