The reprocessing, preservation, and maintenance of the wide historical architectural heritage in Italy represent one of the main challenges of digitalization; not only it is one of the oldest among in Europe, but it is also widespread across the country between cities and rural areas. The care of such an aging built environment needs a carefully planned approach that can take advantage of new technologies such as Historical/Heritage Building Information Modelling (H-BIM) and Digital Twin (DT). The final goal is to promote a long-term sustainable restoration with high qualitative standards. Usually, the topic of sustainability is discussed for new constructions where it is of fundamental importance to save materials, energy, land use and to reduce the carbon footprint. However, being the number of historical buildings elevate in Italy, the concept shall be extended also to them, that are way more fragile if compared to the surrounding. Moreover, cultural heritage is connected to specific challenges that need to be addressed. What was happened in Aquila region after the earthquake of 2019 must not happen again. Digital technologies can be used to prevent such a catastrophic event, preventing and limiting damages, providing evaluable information, and realizing a tool that can be shared among the stakeholders to restore the physical and cultural value of an historical building also in case of extreme events.