With the proliferation of context-less designs internationally stemming from beliefs around progress, development, growth, and the idea that urban design approaches easily travel and can be replicated, this paper argues that urban design might usefully attend more carefully to the local contexts in which it is practicing. Augmenting traditional proscriptive (critiquing poor practice design) and prescriptive (suggesting best practice design) approaches with new critical thinking on culture, to deliver contextually responsive design that is also culturally sensitive. We argue more must be done to analyse and explore contexts where consensual norms around planning practice are frequently absent, such as places characterised by historically embedded cultural sensitivities; emerging out of conflict; or urban informality. This case is evidenced in an exploration of the discursive construction of ‘Homs Dream,’ a development scenario for the future of the Syrian city. The paper concludes with a challenge for urban design, in both theory and practice, to continue developing new thinking at the (dis)junction between urban form and culture.