Chapter 12 analyses the recent institutional reforms of healthcare organizations that led to an increase in the supply chain as well as the population served. As a consequence, some Local Healthcare Authorities (LHAs) have prompted piloting and innovative transitional care (TC) solutions to smooth patients’ transitions between inpatient and outpatient settings. The chapter analyses mature experiences of TC, exploring the solutions under development and identifying the managerial implications for the newly created healthcare organizations. The analysis provides a preliminary literature review that places TC within the recent evolution of discharge management and integrated care services. Regional experiences were compared through four in-depth case studies conducted in Italian LHAs, which were selected as exemplary because of their stage of development within the associated regional healthcare service reforms. The four case include the Service Center of the Health Agency in the metropolitan City of Milan in Lombardy, the community operating center for two LHAs in Veneto (Dolomiti and 8 Berica), and the Agency for Continuous Care of the South-East LHA in Tuscany. The results highlight key elements featured by these new service delivery models: first, TC services are focused on patients with complex health and social care conditions. Second, TC services represent new organizational functions and not units within LHAs, and usually are located in the staff of the managing director responsible for integrating inpatient, outpatient and health and social care. Finally, unlike what has been observed from other the international experiences, the TC models analyzed are focused primarily on the organization. The management of relationships and service integration for complex needs thus calls for innovative care models capable of shifting the organizational and delivery responsibilities from the professionals to the organization, namely from professional leadership to organizational capacity and accountability to provide integrated care pathways.