This study critically examines Tanzania's re-entry programme for teenage mothers through a critical theory lens, arguing that formal policy inclusion masks continued structural marginalization. Employing a qualitative multiple-case study design across four secondary schools in Dar es Salaam, the study engaged 28 participants, including school heads, teachers, programme coordinators, matrons, and teenage mothers. Theoretically grounded in critical theory and intersectionality, the analysis reveals that institutional strategies intended to support re-entry into special classrooms, flexible schedules, dedicated staff, and counselling simultaneously enable access. Support services address symptoms rather than the root causes of marginalization. Teenage mothers face intersecting barriers, including stigmatization, inadequate parental support, multiple responsibilities, community resistance, and facility inadequacies. The study concludes that the re-entry programme reproduces rather than dismantles exclusionary power structures. Transformative recommendations include community consciousness-raising, challenging patriarchal norms, structural interventions addressing poverty and gender inequality, and policy reforms centring teenage mothers' agency.