Urban drainage systems have existed as a vital city infrastructure to collect and convey storm water and wastewater away from urban areas. Despite development over the years, it remains a significant challenge to design sustainable and effective functioning of drainage system. This study assessed the approach to drainage system sustainability in Woliata Soddo town. To this end, households of the town and public sector officials were interviewed to obtain necessary information for the study. Inadequate coverage, poor quality and inappropriate provision of drainage infrastructure were problems identified in the study. Weak technical and institutional capacities associated with lack of finance, lack of integration among concerned bodies, lack of community participation and poor operation and maintenance are factors constraining proper drainage infrastructure provision and worsening the situation in the study area.