As cash transfers have become key tenets of social protection systems in the global South, much effort has gone into evaluating their outcomes. Less attention has been paid, however, to young beneficiaries’ experiences of cash transfers and the contextualised and differentiated impacts on their lives at the micro-level. Based on a qualitative study of young recipients of Brazil’s Bolsa Família programme, this article explores the factors that shape young people’s schooling trajectories. The article demonstrates the complexity of young people’s lives vis-à-vis the CCT policy model; particularly, how their trajectories do not conform to its linear logic, but rather reflect a more complex interaction of gender norms and social and economic inequalities. The tension between the linearity of the policy model and these differentiated and gendered trajectories in turn complicates how young people navigate the transition to social adulthood, by marking out ‘problematic’ vs ‘successful’ transitions and trajectories.