For young people, the end of secondary school represents a critical transition point. This article aims at understanding how schools support a particular group of disadvantaged students to transition into education, training, or employment. Drawing on a life-course perspective and with refugee-background African students as an empirical focus, this qualitative case study documents career support practices in nine government schools in the State of Victoria. The findings show that schools provide transition opportunities that support African students to envision their post-school educational and career trajectories. The arrangements include career planning, alternative pathways, and employment of community engagement officers. However, there are persisting challenges that impede this group of students from fully benefiting from these arrangements. The main barriers identified here are academic disengagement, doxic aspirations, misconceptions about qualifications, and low self-efficacy. The article also argues that the persistence of these challenges is attributable at least in part to such overlooked factors of engagement as institutional practices, student agency, and home environment.