The purpose of this paper is to explore the links between the experiences of parents and youth within racialized immigrant families to gain a better appreciation of intergenerational dynamics, drawing on interviews and preinterview surveys with 47 immigrant youth and their parents. Our thematic analysis of data explores the diversity of families' immigration experiences, labor market challenges for parents, shared family discourses of sacrifice and opportunity, and differences in youth responses to the high expectations of parents. We conclude that the life course transitions experienced by parents have important consequences for their children; immigrant youth feel a strong sense of intergenerational obligation, and this obligation is problematic for a significant minority of youth. Our qualitative findings thus temper the optimistic picture of these youth presented in large-scale studies of their aspirations and attainment.