Schools in Australia are required to promote equitable access to education and provide support services to students with chronic health conditions (CHCs). This qualitative study was conducted to explore stakeholders' experiences and perceptions regarding school-based support. In-depth interviews were conducted with 38 parents of upper secondary school students with cystic fibrosis, anorexia nervosa or cancer (which were illustrative of different types of severe congenital, mental health or somatic CHCs). This enabled comparison of findings to determine whether there were any patterns in perceptions and experiences that were tied to the different CHCs. Data were analysed using a modified grounded theory approach to identify themes. Even though analysis indicated that all cohorts of parents viewed informed educators as best placed to provide tailored school-based support, major cohort differences were reported in parental experiences of school-based support as well as parental diagnosis disclosure behaviour. This latter finding was associated with cohort-related perceptions of risk to their adolescent child. Barriers to school-based support were perceived as varying by condition, the advocacy experience of parents and the nature of health service supports. Taking these findings into account, modification of current policies and practices within education and health sectors may lead to more equitable educational outcomes.