Choosing a secondary school represents an important step in the lives of students in Italy, in that it has a strong bearing on their ultimate educational achievement and labor force trajectory. In this article, we analyze the effect of generational status and length of residence on the transition to secondary school among immigrants living in Italy. Using data from the ITAGEN2 follow-up, we analyze scholastic results from the middle school final exam and the choice of secondary school among the adolescents in Italy. Children of immigrants are more likely to have inferior outcomes on the middle school exam and to enroll in vocational and polytechnic schools. Our multivariate results indicate that, after controlling for the family’s human capital and other key background factors, immigrant students show greater propensity to choose a vocational path. Differences between immigrants and natives in secondary school tracks are also manifested when previous scholastic results are taken into account.