How do the educational trajectories of young people develop differently at the transition between lower and upper secondary education and training--even amongst students labelled as disadvantaged with regard to social background, gender or ethnicity? The aim of the article is to understand the role of decision-making in the emergence of educational trajectories. Based on the analysis of qualitative interviews with students from schools in disadvantaged areas, patterns of educational trajectories are discerned with regard to the ruptures they involve, the destinations they take and the degree of choice young people have. The in-depth analysis of exemplary cases, however, reveals that even within similar patterns of trajectories decision-making processes occur in different ways. Therefore, constellations of decision-making are elaborated which cross-cut the patterns of educational trajectories. The fact that both institutional structures of different education systems and individual biographical orientations do make a difference reveals the complexity of educational trajectories in the interplay of structure and agency.