Increasing numbers of Cigano people in Portuguese schools show that this is the most educated generation to date. However, according to recent data only 2.6% are enrolled in secondary education. Using an intersectional approach examining gender, ethnicity, and family socioeconomic status to explore the youngsters' academic trajectories, and focusing on tensions of the interplay between structural constraints and individual agency, enables us to explore identity reconfiguration processes ('in-between'). The data, based on 32 semi-structured interviews, point to three main dimensions regarding the youngsters' aspirations for social mobility: the school relevance to achieve jobs differing from traditional activities; school perceived as a means to develop important transversal skills, useful in broader citizenship contexts; school as a privileged space for inter-ethnic socialisation, with impact on the youngsters' school and professional future. Participant heterogeneity explains variations in their aspirations for upward mobility, as well as differentiations in the construction processes of in-between identities.