This article discusses recent urban development in two cases, Imizamo Yethu, South Africa, and Tai O Village, Hong Kong, within transition design frameworks. The article builds on contemporary theories that suggest categorical distinctions between urban population centres and that less dense hinterlands support adverse normative relationships in the context of continuous economic, administrative, political, and other transitions. It introduces the premise of “centre-hinterlands,” to describe conditions where hinterland conditions are found within the centre and where researchers can construct provisional, administrative, and economic difference as inequity. The article presents research in Imizamo Yethu and Tai O that elaborates this description. The main methods applied in Imizamo Yethu include a morphological study and field observation, and the key findings in Imizamo Yethu include the gradual loss of distinction between “formally and informally” developed parts of the settlement in morphological character, developmental model, and administration. The main methods applied in Tai O Village include stakeholder workshopping, conducting a survey and interview, and a short-term pedestrian traffic monitoring project. The key findings in Tai O include economic and behavioural patterns that economically and socially entangle the village with the surrounding region. The article concludes with a discussion of transition design frameworks’ relationship to potential for radical change in each development case.