Students with Special Educational Needs and Disabilities encounter complex and circuitous transitions from post-primary settings to Higher Education. In Ireland, inequitable access to Individual Education Plans, and a lack of policy infrastructure to provide formal transition planning, means that these journeys are varied and uncertain. This study presents findings from surveys completed by parents supporting students with disabilities in their final 3 years of mainstream secondary school (n = 69), and in-depth interviews with a self-selected subset of parents (n = 8). Results point to: (i) disparate levels and quality of support and guidance, (ii) fissures in communication channels between parents and schools, (iii) insufficient awareness and understanding of the interplay between disability and successful post-school outcomes, and (iv) high levels of stress, anxiety and frustration experienced by students, parents and carers.