In the last decade, the dramatic developments in digitalisation have reached cultural heritage. Digital archiving and reconstruction, virtual reality, and 3D laser scanning, modelling and printing, are influencing the way we consume, manage, and preserve it. As part of the latter, detailed virtual records of endangered urban cultural heritage, through digital archiving, capturing, and reconstruction techniques, can help preserve its memories and lengthen its life; particularly, once decision-makers resolve to end its tangibility. However, the application of digitalisation to cultural heritage is not always easy, faced with issues such as cost, lack of sources and skills, sustainability, and intellectual property limitations. This paper illustrates the challenges encountered by land-deprived and fast-growing Southeast Asian cities in amalgamating urban cultural heritage preservation with pressing development needs. Ultimately, it discusses the introduction of digitalisation in this debate by examining the broader consequences of the association.