Cultural heritage has always been recognized as a fil rouge that links the past, present, and future. Today more than ever, its existence is threatened by natural disasters, conflicts, and vandalism that have a serious impact on the entire urban fabric. Digital technology and community engagement can contribute to its safeguarding as well as to “re-generating” urban spaces and giving life back to the cultural identity that may have been lost due to disaster or war. In this perspective, rebuilding the urban spaces after a traumatic event represents a key strategy for resilience, providing cities and communities the opportunity to reinvent themselves. To this end, the paper intends to show that adaptive reuse of built heritage, when properly supported by digital technologies and collaborative and co-design multidisciplinary participatory processes, can be an effective strategy for renewing and thus preserving memories of built heritage damaged by disasters or armed conflict. The analysis of best practices for adapting historic buildings, especially those repurposed after wartime damage, clearly supports this point.