In recent years, AUSL Romagna has taken on a prominent role in implementing regional digital health strategies, adopting a proactive and experimental approach that, while dynamic, has not been without challenges. This article traces the organizational and strategic evolution of the organization in the field of digital transformation, focusing on the level of development and maturity of telemedicine initiatives currently active in the territories of Rimini, Forlì, Cesena, and Ravenna. The initiatives reviewed – from heart failure management to diabetic telemonitoring, from wound care pathways to platforms for multidisciplinary oncology consultations – reflect a highly varied landscape in terms of progress, consolidation, and integration into care pathways. The case study highlights a dynamic environment, driven by numerous high-potential projects often initiated by individual clinicians, yet still fragmented and not always coordinated. The challenges ahead involve not only the structured and consistent integration of digital services into clinical pathways across the territory, but also the strengthening of internal governance and the promotion of a widespread professional culture of technological innovation. The experience of AUSL Romagna thus offers valuable insight into both the opportunities and the critical issues that must be addressed to make telemedicine a structural and truly operational component of healthcare services.