The experience of Hospital Schooling and Home Education in Tuscany is currently at a crossroads. On one hand, years of work have produced well-established practices and a network of relationships between schools, hospitals, and local communities; on the other hand, the increase in demand and the growing complexity of cases require an organizational and cultural leap in quality. Through direct analysis of the USR coordination and the work carried out in schools, it emerges that the transition from emergency management to structured planning is still incomplete. The new Regional Technical Committee and the network of Health-Promoting Schools represent promising tools, but the real challenge remains cultural. It is necessary to move beyond a logic of mere compliance and embrace an inclusive vision that considers illness as a possible part of the educational journey.