Recent evidence suggests that academic performance following the transition to high school may serve as a critical juncture in determining future success for African American boys (Roderick, 2014). A great deal of the education literature examining the experiences of African American boys focuses on the myriad ways in which this population is disadvantaged in school systems. While these outcomes are crucial to understanding African American boys’ educational trajectories they do little to account for how African American boys themselves interpret and respond to academic environments, especially following such an important transition. The concept of academic engagement, however, offers an opportunity to examine the means by which students make sense of, identify with, and respond to their academic environments. By examining the experiences of African American boys through this lens, this dissertation asks: What is the relationship between African American boys’ perceptions of their academic environments and their academic engagement following the transition to high school; and how does this relationship affect their academic outcomes in the critical 9th grade year? Answering these questions has the potential to provide researchers and practitioners alike with a more in-depth understanding of academic performance and outcomes for African American boys broadly.