The authors conducted a study to address gaps in the literature regarding parents' experiences of the transition of their child from special education to postschool mainstream services. Specifically, this study sought to explore the nature, factors, and psychological impact of their child's transition to post-school services. To achieve these aims, a qualitative, grounded theory approach was employed in which semi-structured interviews were conducted with a small sample of parents of children with mild intellectual disability living in the southern region of Ireland. The results indicated that the transition process was generally experienced as stressful, uncertain, and problematic, particularly in terms of the bureaucratic aspects. The experiential shift from school to vocational training and employment emerged as the most salient in parents' perceptions. Parents also identified a range of factors that served as barriers and supports of the transition process, in which the role of the parent emerged as a key facilitative factor. The findings suggest that considerable gaps remain between policy and service provision in Ireland regarding transition planning and postschool services for young adults with intellectual disabilities and their families, often posing barriers to successful transitions.