Abstract Italy’s healthcare sector has undergone significant digital transformation since 2008, driven by national strategies and reforms overseen by the Ministry of Health, the Ministry of Economy and Finance, and the Agency for Digital Italy. Key initiatives include the establishment of centralized booking systems, electronic health records (EHR), ePrescription, dematerialization of medical reports and disease certificates, patient summary, and telemedicine services. Despite regional variations, progress in the EHR adoption has been notable. Ongoing investments under the 2021 National Recovery Plan aim to further enhance digital healthcare infrastructure by 2025 through the involvement of the Italian National Agency for Regional Healthcare Services (AGENAS). Currently, Italy monitors progress through comprehensive measurement frameworks tracking digital health initiatives’ implementation and impact. These encompass indicators reported quarterly by public healthcare facilities regarding the implementation of patient portals, regional registries, network infrastructure, regional EHR systems (i.e., n° of users), and digital laboratory reports. In parallel, we conducted a cross-sectional survey assessing knowledge, opinions and concerns among primary care physicians (PCPs) following the 2022 reform, which introduced Community Hospitals, Community Houses, and telemedicine in primary care. The survey highlighted mixed opinions and insufficient knowledge among PCPs regarding the novelties. Clearer communication and coordination with territorial services appears necessary. Many GPs are engaging in telemedicine, but digital literacy gaps remain, as only 35.7% believed they had necessary digital literacy. This is an insight into Italy’s digital health roadmap, mainly involving primary care and focusing on achievements, challenges, and future prospects in utilizing digital solutions across healthcare settings.