<p>The growing availability of big data and digital planning tools offers new ways to understand, analyse and design cities. Urban design pedagogy has accordingly adapted, embracing new analytical tools and methods to study the built form, including computer-aided design and parametric modelling. This paper investigates how procedurally modelled shape grammars can operationalise theoretical concepts of urban elements, patterns, morphological studies to inform design proposals. This investigation is based on an empirical study of an urban design studio conducted in Singapore where human-centric design principles were translated into computational logic for design synthesis. Through qualitative observations of the CGA modelling for urban design, the translation process and points of friction encountered are documented, offering new insights for urban design pedagogy and software development in the context of high-density Asian cities.</p>