Despite their average high levels of educational achievement, Asian American students often report poor psychological and social adjustment, suggesting an achievement/adjustment paradox. Yet, the reasons for this paradox remain unclear. Drawing on 5-year longitudinal qualitative interview data, this paper compares the family dynamics of two groups of adolescents from Chinese immigrant families: non-distressed adolescents (n = 20) who have high levels of academic achievement and high levels of psychological well-being; and distressed adolescents (n = 18) who have high levels of academic achievement but low levels of psychological well-being. Findings suggest that the two groups of families differed in parenting approaches after migration, parent-child communication, parental expectations, and parent-child relations. Implications for Asian American adolescent and youth development are discussed.