One of the primary objectives of Italy’s ultra-broadband strategy is to create a high-performance network infrastructure with widespread coverage of the territory, guaranteeing fast, stable, and secure connections for citizens, businesses, and public administrations. The intent is to allow the digital divide to be overcome, creating high-performance connective networks even in areas with total or partial market failure. At the same time, the strategy aims to promote social and territorial cohesion, improving access to digital services such as those related to education and health, as well as all other services provided by the Public Administration. By anticipating and encouraging private investments in carrying out major projects, also through favorable regulation and support for sustainable business models, another objective of the strategy is to increase the country’s competitiveness, making investments more attractive. This research explores the main actions taken by Italian governments for the involvement of private entities, along with the key issues of adoption, sustainability, and implementation times in the context of ultra-broadband infrastructure projects. Finally, the research culminates with the analysis of how a careful application of project management principles could have mitigated the problems inherent in such ambitious and complex plans.