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.