Increasing numbers of young people experience disruption to their schooling owing to chronic illness. Absence from the day-to-day life of their school for prolonged or accumulative periods of time can erode their sense of belonging and create anxiety about falling behind academically. Maintaining positive connections to school can meet their desire for normalcy and realisable educational goals. Part of a project called Link ‘n’ Learn, funded by an Australian Research Council Linkage grant (2008–2010), this in-depth qualitative case study of 22 participants — senior secondary students and their mathematics teachers — investigated academic continuity: students’ access to and utilisation of opportunities to learn effectively so that academic progress is made despite disruption to full-time schooling. The students experienced diverse types of chronic illness, medical interventions, and patterns of absence from school. They all sought to continue their school studies. Their teachers highlighted surprise, concern and discomfort related to students studying during serious illness, and school workload issues. Ambiguities about educational responsibility for students during absence were widespread. Teachers demonstrated hesitance to initiate contact with students, but students nevertheless expressed their desire for teachers to remain involved with them. Implications for the educational support of young people with chronic illness are presented.