Based on a longitudinal sample of 1,452 African American and European American adolescents and their parents, parenting practices (i.e., monitoring, warmth, and autonomy support) at 7th grade had significant indirect effects on college enrollment 3 years post high school, through their effects on aspirations, school engagement, and grade point average (GPA). All 3 parenting practices were related to aspirations and behavioral engagement at 8th grade, with 2 of the 3 parenting practices related to the emotional (monitoring and warmth) and cognitive (autonomy support and warmth) engagement. The reciprocal relations between aspirations and engagement/GPA were significant, although the effects from 8th aspirations to 11th engagement were stronger than the reverse path. Ethnic differences were found only for parenting practices: monitoring had stronger associations with GPA and behavioral engagement for African Americans, whereas autonomy support had stronger associations with GPA for European Americans. For African American parents, a delicate balance is needed to capture the benefits of higher levels of monitoring for promoting GPA and behavioral engagement "and" the benefits of autonomy support for developing aspirations and cognitive engagement. Parental warmth was equally beneficial for supporting aspirations, engagement, and achievement across ethnicity.