Social development may vary depending on contextual factors, such as attending a day school or a boarding school. The present study compares students from these school types with regard to the achievement of specific social goals, perceived social support, and reported prosocial behaviour. A sample of 701 students was examined. Students from boarding schools reported higher success in gaining autonomy from parents and forming romantic relationships than students from day schools. However, adolescents from day schools reported higher levels of peer-group integration than students from boarding schools. Compared with students from day schools, students from boarding schools perceived more support from their teachers, but less support from their parents. No difference in prosocial behaviour was found between the two groups. We conclude that some students from boarding schools need support in gaining access to a peer group. In addition, measures are suggested for promoting parental support of students from boarding schools.