Acknowledging the pivotal importance of education in steering individuals’ life courses, this chapter focuses on children of immigrants’ upper secondary school choices and on how they are affected by institutional settings. Preliminary results do not yield support to the hypothesis suggested by the psychological literature that the direct experience of a migration negatively affect educational investments as a result of a reduction in student’s sense of self-efficacy. Instead, both students’ participation in full-time education and the attended field of study differ on the basis of the ethnic background, as suggested by previous sociological studies. It is interesting to note that the influence of ethnicity has a positive sign: when students with similar socio-economic resources and similar grades are compared, ethnic minority students tend to overperform the ethnic majority. Despite the fact that ethnicity is commonly associated with increased motivation and thus more prestigious educational choices, eventually initial lower academic achievements (due to differences in cultural assets between ethnic minorities and the majority) could depress educational decisions. Here is where the country-specific educational system exerts its greatest impact. The findings suggest that comprehensive educational systems that are typical in Anglo-Saxon countries (labelled as “choice-driven”) are more beneficial for ethnic minorities than the highly stratified and selective systems of central Europe, where previous grades bound successive choices, giving less room for expression to ethnic minorities’ higher aspirations.