This study examined longitudinally sequential pathways between parental socioeconomic status and immigrant children’s school performance and depressive symptoms during adolescence, as well as educational attainment and self-rated health upon transitioning into young adulthood among three immigrant groups. Participants included 1522 immigrant youth (M age = 14 years) and their parents. The youth were assessed at three time points (1992, 1995, and 2002). The parents were assessed at time 2. The mediating effects of intergenerational transmission of educational expectations and parent-child conflict, and the moderating effects of parental school involvement were also examined. The findings showed that lower levels of parental school involvement combined with higher levels of parental educational expectations were associated with increased depressive symptoms in adolescence and diminished self-rated health in young adulthood among Asian youth composed of Chinese, Koreans, and Filipinos. For Latino youth from Mexico and Central America, intergenerational transmission of educational expectations mediated the effects of parental SES on youth’s GPA in adolescence and educational attainment in young adulthood only among those who reported high levels of parental school involvement. Findings showed that family mechanisms operated differently across immigrant groups and contributed to variations in immigrant youth’s adjustment outcomes in both adolescence and young adulthood.