The archaeology of our built heritage is centred on the understanding of human experiences, rituals and social history that add meaningful narratives to physical fabric, structures and artefacts. The meaning of the building in the collective memory is intrinsically attached to the process by which it was produced and the manner with which it endured a series of critical socio-cultural change. Whilst we cannot live in the past, engaging with historic buildings or walking through traditional urban fabric and alleyways becomes an essential asset of the contemporary urban experience. This paper interrogates the dilemmas of authenticity, originality and legitimacy of the preservation of architectural and urban heritage through digital and virtual technologies. It addresses examples of historic buildings that have changed character, functions or got destroyed during times of wars and conflict. With advanced techniques of recording historic buildings through digital and virtual environments taking a leading role in modern preservation, integrating architectural heritage into the creative economy and income generating activities is critical to their survival in the digital age.