Uganda has an increasing number of vulnerable youth in care who require support to transition into adult life. This article explores the agency enablers and the factors which hinder adolescents and emerging adults transitioning from care to adulthood, with an emphasis on the transition into work taking a case study of the Uganda Youth Development Link. Cross-sectional and case study designs were employed using structured questionnaires, focus group discussions, and in-depth interviews. Results show that care programs helped care leavers gain skills that facilitated self-reliance through employment in the formal sector and self-employment, a savings culture and expansion of social networks. Enablers included the mentors, exchange learning visits, placements with businesses, and positive social support networks. Unaffordable business premises, stigma and discrimination, limited access to credit, and insecurity inhibited successful post care transition. The conclusion emphasizes the importance of agency and structure in the transition out of care in Uganda.