For students with emotional and behavioural issues the bridge from middle years to senior years can be particularly challenging. This transition is especially problematic if the students are moving from self-contained or specialized programming supports in middle years to inclusive senior years environments. This qualitative research study examined the perspectives and experiences of four principals and three student services personnel regarding the transition of students from specialized middle years placements to inclusive senior years schools. Each participant was asked their opinions on what strategies, structures, policies and supports assisted with the transition process as well as those that detracted from successful transitioning. Qualitative analysis of the data suggested that students need to connect with a positive adult upon transitioning to senior years, and they need to perceive that their senior years school is a safe and positive place for them to attend.