If today there exists a single transcendent idea about the family-school connection, it is that a positive parent-child relationship improves children's chances of succeeding in school. However, using data from the Texas Higher Education Opportunity Project (N = 5,836), we demonstrate that, although positive parent-child relations are associated with better academic achievement in high school, they also are associated with an increased desire to live at home during college, which in turn decreases students' chances of enrolling in a 4-year college. Furthermore, we replicated some of these associations using the National Longitudinal Study of Adolescent Health (N = 10,120), demonstrating that positive family dynamics can influence educational outcomes in potentially divergent and unanticipated directions.