Water Sensitive Design (WSD) is gaining attention as a Nature-based Solution (NbS) to urban water problems. It incorporates green infrastructure with engineered urban water systems through innovative design of the built environment and urban landscape. In Africa, Johannesburg and Cape Town are two cities engaging with WSD at a policy level. This paper uses the Strategic Niche Management (SNM) approach in a comparative analysis of ongoing engagement with WSD in Johannesburg and Cape Town. We explore the extent to which this engagement signals the launch of the transition towards water resilience. WSD represents a niche that is in synergy with the visions of sustainable urban (water and environmental) management in both cities. Results indicate a progressive engagement with WSD by different actors at regime and niche levels. However, the lack of coordination and capacity deficiencies due to limited social networks and higher order learning are challenges that constrain take-off and further consolidation of the WSD approach in the transition towards water resilient futures. Furthermore, we find urban governance practitioners struggle with reconciling the pursuit of visions of sustainability to be realised through nature-based urban development with the pressing infrastructure deficits that persist in most African cities.