The digital transformation of Italian healthcare organizations has experienced a significant acceleration during the implementation of the National Recovery and Resilience Plan (NRRP), particularly through the investments of Mission 6. Building on previous research conducted by FIASO (Italian Federation of Healthcare and Public Hospital Companies) and CERGAS (Centre for Research on Health and Social Care Management) SDA Bocconi this study provides an updated overview of the digitalization process within the Italian National Health Service (SSN), highlighting both technological advances and organizational implications. A longitudinal comparison between two nationwide surveys (2022 and 2024) was carried out on a sample of 19 public healthcare organizations to assess progress in the adoption of digital systems. Findings reveal substantial improvements in digital infrastructure and system informatization, though with uneven implementation across organizations. The analysis underscores that digital transformation effectiveness depends not only on financial resources and technology availability, but also on organizational governance, strategic prioritization, and workforce digital skills. As NRRP investments near completion, ensuring the sustainability of these innovations will require reinforcing digital competencies, strengthening monitoring and evaluation systems, and fostering organizational learning processes to embed digitalization as a continuous transformative driver for equity, efficiency, and sustainability in the SSN.