Risk-sensitive development is required to reduce risk that has accumulated in the city and to better consider risk when planning new developments. To deliver a sustainable city for all requires a more frank and comprehensive focus on procedure: on who makes decisions, under which frameworks, based upon what kind of data or knowledge, and with what degree and direction of accountability. Acting on these procedural questions is the promise of transformative urban development. This paper explores the status of risk sensitive and transformative urban development and scope for transition towards these components of sustainability in urban sub-Saharan Africa through the lens of diverse city cases: Karonga (Malawi) Ibadan (Nigeria;), Niamey (Niger and Nairobi (Kenya). The paper draws from a three year research and capacity building programme, Urban Africa: Risk Knowledge (www.urbanark.org) that aims to address gaps in data, understandings and capacity to break cycles of risk accumulation. A common analytical framework is presented to help identify blockages and opportunities for transition towards a risk-sensitive and transformative urban development. This framework is then illustrated through each city in turn and a concluding discussion reflects on city observations to draw out recommendations for city level and wider action and research partnerships.