Study 1 examined the relationships between parental attachment, academic achievement, and psychological distress among a multiethnic sample of academically successful inner-city high school students (19 White, 54 Black, 9 Asian, 18 Hispanic). These students participated in an enrichment program designed to prepare high school students for college success. The results suggest that the affective quality of maternal attachment is positively associated with grade point average, and the affective quality of paternal attachment is negatively associated with depressive symptoms. In Study 2, case examples provide an examination of sources of support, life stress, and patterns of resilience. Implications for prevention and intervention are also discussed.