How do health professionals and teachers make decisions about supporting young people whose lives are disrupted by chronic health conditions to stay in touch with schooling? Analysis of the interview and focus group data from health and education professionals who participated in the "Keeping Connected" project reflected common family-focused orientations in supporting young people in their care. However, their practice ideals appear to be compromised by institutional constraints such as inflexible hospital policy and treatment schedules, and rigid criteria and lack of clarity associated with disability funding for support in schools. These constraints have implications for policy-makers in terms of how knowledge and evidence about supporting these young people might be communicated more effectively within and across the health and education sectors.