The transition to middle school is often marked by decreased academic achievement and increased emotional stress, and African American children exposed to social risk may be especially vulnerable during this transition. To identify mediators and protective factors, the authors related severity and timing of risk exposure to academic achievement and adjustment between 4th and 6th grade in 74 African American children. Longitudinal analyses indicated that severity more than timing of risk exposure was negatively related to all outcomes and that language skills mediated the pathway from risk for most outcomes. Transition to middle school was related to lower math scores and to more externalizing problems when children experienced higher levels of social risk. Language skills and parenting served as protective factors, whereas expectations of racial discrimination was a vulnerability factor. Results imply that promoting parenting and, especially, language skills, and decreasing expectations of racial discrimination provide pathways to academic success for African American children during the transition from elementary to middle school, especially those exposed to adversity.