In this study, we examine students' educational attitudes upon the transition to Dutch senior vocational education (SVE), a transition associated with high dropout rates in the first year. Prior studies have identified differences in educational attitudes between sociodemographic groups. However, the mechanisms underlying those differences remain topic of debate: some studies point at differences in the school orientation and support in students' social communities outside school, others focus on differences in educational experiences between sociodemographic groups. Multilevel sequential regression analyses on a diverse sample of 1438 students in urban SVE schools reveal that students have very positive educational attitudes upon their transition to SVE. Ethnic minority students express particularly positive attitudes. School-related encouragement and support at home plays an important role in students' attitudes, but the attitudes of students from lower educated or ethnic minority communities are less related to this support. Prior school experiences play an essential, but occasionally counterproductive, role in students' attitudes upon transition, depicting the transition as a fresh new start for some, and an unwelcome threshold for others. (Contains 2 tables and 2 figures.)