The different school forms within Germany's tracked education system have traditionally led to different diplomas and thus future education and work prospects. Tracking has persistently disadvantaged migrant youth, who are over-represented in lower tracks. Since a 2010 reform introduced a two-pillar model in city-state Hamburg, the two remaining secondary-school forms, "Gymnasium" and "Stadtteilschule," both offer the university-entrance qualification ("Abitur") but remain socioculturally segregated. Based on 14 months of multi-sited ethnographic fieldwork (Ghana and Germany), this paper explores how Ghanaian newcomers who want to obtain the "Abitur" strategically navigate Hamburg's secondary-school system. The paper argues that the two-pillar model creates space for newcomers to consider factors beyond diploma accessibility in their educational trajectories, namely academic and sociocultural factors, thus leading to varied, and sometimes unexpected, pathways to reach their goal. Further, it demonstrates the value of youth-centric and transnational research approaches for revealing newcomers' agency in strategically navigating their educational trajectories.