Scholars of social determinants of health have long been interested in how parents’ (origin) and adult children’s educational attainment (destination) influence health behaviors and outcomes. However, the heterogeneous effects of origin and destination on health—that is, education conveys health benefits for what socioeconomic group—remain unclear. Because of selection and interdependent pathways, a standard regression model is not suitable for addressing this question. Using clearly-defined estimands and multilevel models, we analyzed data from the Panel Study of Income Dynamics to investigate the heterogeneous and dynamic effects of origin and destination education over the life course on multiple health outcomes. We found that the protective effects of college education against risky behaviors and negative health outcomes were remarkably similar regardless of father’s or mother’s educational attainment. In contrast, parent’s education appeared to have a larger effect when children’s education level is lower. Our results also suggest distinct life-course patterns among the health variables examined. We conclude by discussing the policy implications and future directions.