This qualitative combined methodology study was undertaken to identify key factors in re-engagement by students aged 18-21 years returning to Secondary School. It was conducted in classrooms providing educational programming for students in treatment, care, custody or correctional facilities. An interview approach was adopted since continuous intake and provision of programming year round did not permit an intervention-based design. Six recurrent themes emerged from analysis of student responses: the importance of classroom climate; the need for intellectual engagement; the centrality of the student-teacher relationship; the value of alternative educational programming; the role of psychosocial factors; and the influence of school-level elements such as class size. These recurrent themes indicate system-based contributors to disengagement and academic failure that can be modified. Curriculum relevance, teacher role, teacher-student relationship and institutional flexibility around programming were identified as key contributors to student engagement.