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Including a courtyard open to the sky is an interesting design feature in most old town shophouses. It has been found that the courtyard shophouses in this urban fabric were always good examples for the bioclimatic typologies where their residents could enjoy the outdoor daylight and fresh air with a minimum of energy use while not being separated from their climate and culture. However, such courtyards in Taiwan have gradually disappeared while more have been retained in urban Southeast Asia. This thesis intends to determine what kinds of factors influence the application, outcomes, and changes over time of early shophouses for its dwellers. The principal aim of this thesis is to evaluate the potential of the retention of traditional shophouse courtyards in urban Southeast Asia, especially in Taiwan, with a focus on the preservation of continuity rather than the preservation of the past. The work presented in this thesis consists of three main research activities, all focusing on the use of simulation tools and the logic of reasonable inferences to support the continuance of traditional shophouses: analysis of current traditional shophouses; development of an approach for well-founded selection of ecological design in lighting and ventilation; analysis of the suitability of existing practices and experiences to support the selection process; and development of a strategy as well as a proof-of-concept prototype that provides support for the selection of ecological issues and that demonstrates the viability of the proposed changes. It should be noted that the research is exploratory in nature and has only begun to address the many issues that are important in the preservation of urban heritages, but the questions addressed – what quality needs are important for shophouse occupant satisfaction and what quality dimensions are important for public attitudes – are arguably among the most important in quality maintenance.