This research explores the frequent urban flooding problems typically experienced in South-East Asian cities. Heavy rainfall during the monsoon period in combination with rapid urbanisation in the past decades causes an increasing amount of inundation events in the case study area Hanoi. The damage caused by these floods results in major economic losses that affect local citizens as well as governmental authorities. Flood waters are often heavily polluted with sewer water, threatening public health and reducing the overall livability of Hanoi. In addition, inundated streets are difficult to navigate, and waves induced by vehicles can lead to dangerous situations for pedestrians and other road users. This research aims to have a better understanding of the failure mechanisms of Hanoi’s drainage system, and the risks associated with each mechanism. Since there is no standard methodology for probabilistic risk assessment of urban drainage systems, the methodology for levee assessment was adopted and adjusted to the field of urban drainage. This straight-forward method is transferable to other study areas and results in clear and comprehensive fault trees which are easily interpreted by drainage authorities. A combination of expert judgement, qualitative fieldwork and analysis of newspapers was used to obtain an overview of all failure mechanisms and presented in the form of a fault tree. To investigate the potential damage that could be done by each failure mechanism, a probabilistic risk assessment was done using the urban drainage modelling software PCSWMM, and the potential risk of each mechanism was quantified. For the mechanisms with an unacceptably high risk, potential solutions were proposed. Four failure mechanisms were found that pose an unacceptably high risk on the drainage system: increased catchment size, pipeline blockage, inaccessible drains, and design inaccuracies. Potential solutions are to incorporate Low Impact Development (LID) in the urban area such as green and blue roofs, infiltration trenches and rain barrels. This type of infrastructure reduces the hydraulic load on the drainage system by reducing the runoff peak. In this way, urbanisation goes hand in hand with preserving the natural flows. Other recommended solutions are to revise the cleaning schedule to make it more efficient, and raise awareness among local inhabitants to enlarge their role in the functioning of Hanoi’s drainage system.