Pluvial flood risk is increasing in urban and rural areas due to changes in precipitation patterns and urbanization. Pluvial flooding is often associated with insufficient capacities of the sewer system or low surface drainage efficiency of urban areas. In hilly areas, hillside runoff additionally affects the risk of pluvial flooding. This article introduces a methodical approach and related evaluation criteria for a systematic analysis of potential causes of urban pluvial flooding. In the presented case study, the cause of pluvial flooding at two selected sites in a hillside settlement is investigated based on a coupled 1D/2D model of the whole hydrological catchment. The results show that even though bottlenecks in the sewer system are important, the effect of low surface drainage efficiency and hillside runoff greatly influence pluvial flooding. The knowledge of different causes of flooding can be further used for selecting and positioning appropriate adaption measures. The presented approach proved its practicability and can thus serve as a guidance and template for other applications to gain better understanding and knowledge of local specific pluvial flooding events.