The understanding of the changing nature of recurrent and widespread urban flood risks across the rapidly urbanising Sub-Saharan African cities has, for long, been overshadowed by more general factors such as rainfall intensity, insufficient drainage systems, occupation of floodplains and, more recently, the climate change praxis. Yet, the impact of context-specific conditions on urban flood risks is still surrounded by ambiguity across the existing empirical research, policy and political arena. This research seeks to unveil the missing links regarding how contextual drivers of urban flood risks are understood across urban actors. Using Kampala city as the case study area, this research adopts multi-methods such as key informant semi-structured interviews, web-based surveys, GIS and policy reviews to gather relevant empirical data. The findings indicate that a) the nature of urban flooding is dictated by the level of interaction between socioeconomic, institutional, environmental and infrastructural factors and b) the negligence, ambiguity and inconsistency that characterise the institutional policy landscape plays a vital role in the co-evolution of urban flood hotspots. Overall, this research contributes to an in-depth understanding of the role of multiple context-specific urban conditions in urban flooding, a fundamental prerequisite for designing robust approaches to flood management.