The transition to high school has been identified as a potentially difficult time in adolescents' lives. Reductions in both academic and social functioning often accompany this transition. While these effects have been documented in urban youth, the move to high school has not been extensively studied in rural minority youth. Toward that end, the academic grades and substance use in ninth grade of 447 (184 male and 263 female) African-American adolescents from two rural counties in a state in the deep South were examined in relation to configurations of adaptation from sixth through eighth grade. Results indicate that individual with consistently positive patterns across middle school had higher grades and lower rates of substance use compared to individuals with persistent difficulties or those that transitioned to problem behavior. Many individuals who improved in their patterns of adaptation had relatively high grades, but also rather high rates of substance use in the ninth grade.