Many students drop out in the first year after a school transition. Most commonly used indicators of an increased risk for dropout reveal little of the mechanisms that push or pull students out of school. In this study, we look at the association of a set of common risk indicators with students' supportive resources and school experiences upon the transition to post-secondary vocational education in the Netherlands. Multilevel regression analyses on a diverse sample of 1438 students indicate that most sociodemographic risk indicators relate to less access to supportive resources for school, whereas personal circumstances outside school that are associated with an increased risk for dropout correlate with negative school experiences. Students from lower educated or poor families and students who use drugs, have debts, or are delinquent score negative in both domains, suggesting that those students make the transition with one foot out the school door. (Contains 2 tables.)