This paper explores primary to post-primary transitions for students with Special Educational Needs (SEN) within mainstream schooling in an Irish context. A questionnaire was distributed to a cohort of sixth class students (n = 58) from four different primary schools in advance of their transfer and results were then compared with a similar cohort of first year students (n = 63) from two post-primary schools following the transfer. The perspectives of the key stakeholders involved in the transition process were gained through questionnaires (n = 10) and semi-structured interviews (n = 5). Findings indicate that while a minority of first-year students experience transition difficulties, students with SEN encounter greater obstacles during this crucial time of transfer with increased anxiety and are more vulnerable and prone to bullying than their typically developing peers. Schools should place greater emphasis on transitions involving those with SEN due to their increased vulnerability.