The digitalization of the Italian public administration has followed a transformative path marked by discontinuous progress and structural challenges. Despite the adoption of digital technologies since the 1990s, Italy has struggled to keep pace with the European average, as evidenced by DESI indicators. Early reforms focused on efficiency and administrative transparency, but a lack of coordination hindered the effective implementation of national strategies. A significant shift occurred with the establishment of the Digital Transformation Team in 2016 and was further accelerated by the COVID-19 pandemic, which boosted the digitalization of key services such as digital identity, electronic payments and data interoperability. The National Recovery and Resilience Plan (NRRP) further strengthened investments in cloud infrastructure, cybersecurity and reducing the digital divide. However, challenges remain, including the modernization of internal processes, institutional fragmentation and the enhancement of digital skills within the public sector. This study analyses the evolution of public sector digitalization in Italy, assessing its impact and effectiveness in terms of efficiency, democratic values and security.