Although the impact of ICT technologies is a relevant topic in scientific debate, the relationship between digitization and organizational processes in social and health care still needs to be explored. In light of these considerations, the article focuses on the possible perverse effects, organizational myopias, and unexpected outcomes that may occur within a complex system, such as the healthcare system. Through a typology of anticipatory governance, we intend to identify the scenarios associated with implementing telemedicine and the so-called «digital health» financed by the Recovery and Resilience National Plan. The typology defines four types of policies: established policies, policies to be consolidated, policies to be redesigned, and policies (momentarily) to be postponed. The research is based on two case studies (Lombardy and Tuscany) that the literature has placed on the antipodes and uses qualitative methodologies based on in-depth interviews. The comparison between the two regions highlights the performative role of technologies and the constraints imposed by the PNRR.