Digital transformation is a complex and resource-intensive phenomenon that is causing disruptive changes at social, economic, and institutional levels. This has contributed to the mounting need for better assessing digital transformation maturity through reliable models/frameworks. Even though research provides several models, they suffer from a lack of internal and external validity. Thus, this paper aims to contribute to bridging this gap by proposing a tentative model and preliminarily testing it in the healthcare domain. Drawing on the extant literature a tentative digital transformation maturity model has been applied to the Italian National Healthcare System (NHS) to test it and describe through a content analysis the main dimensions of Italian NHS digital transformation and its maturity stage. The analysis underlined that the Italian NHS is still proceeding in the journey toward digital transformation maturity. It emerged that the analyzed sector needs further effort to strategically approach the wide transformative potential of digital technologies, paying greater attention not only to those dimensions strictly related to processes’ efficiency, but also to those that imply a deep cultural change, a focus on processes’ participation, and their long-term effectiveness. This study offers some interesting implications for enhancing digital transformation maturity models’ reliability and for supporting both health managers and policymakers in strategically approaching this phenomenon. However, its exploratory nature and the application to one specific domain somewhat limit it. The originality of this paper lies in the new dimensions attached to previous digital transformation maturity models and in its practical application to specific and complex sectors such as healthcare.