Retaining walls are important geotechnical structures used to retain earth at two different elevations on either side of the wall. With the explosion of population in urban areas and lack of available space, retaining walls will be an automatic choice especially in hilly terrain. There have been reports of retaining wall failure either under extraordinary loading conditions or due to poor design and construction. This paper attempts to highlight the effects of poor design and construction quality on the performance of existing retaining walls. Two case studies are discussed for the purpose. The first one is the failure of retaining wall at JSS residential school in Ooty. Possible slope failure due to lack of drainage and loss of vegetation in addition to possible wrong assessment of earth pressure on retaining wall resulted in its failure. The second one is the failure of retaining wall at Police Station in Chamarajanagara due to poor construction and lack of drainage to backfill soil. The purpose of this paper is to introduce the actual failure studies of geotechnical structures with reasons for such failure.