Present study attempts to investigate the possible reasons behind the failure of a cantilever retaining wall with relief shelves, which is located in the heart of Hyderabad city, India. A pressure relief shelf is a finite width, thin horizontal cantilever platform extending into the backfill, which are constructed monolithic with the stem of the retaining wall. Number of such shelves is constructed at regular spacing along the height of the wall. From the limited theoretical studies, it is noted that the provision of relief shelves, extending beyond the rupture surface in the backfill, can considerably reduce the earth pressures on the retaining wall and subsequently increase the stability of the retaining structure. The height of the failed retaining wall ranges from 10 to 13.9 m and retains a loose to medium dense sandy soil backfill, and constructed with 5 relief shelves. After few years of construction, a portion of retaining wall of about 20 m length had collapsed and adjoining 20 m length had severely distressed, immediately after the end of a monsoon. The preliminary post-failure investigation revealed that quality of concrete used in construction was satisfactory, and the construction joints were intact. Cracks due to failure had propagated almost up to the full thickness of reinforced concrete wall. To get more insight about the causes of failure, numerical analysis of retaining wall with pressure relief shelves is carried out using widely used geotechnical numerical code, FLAC3D. From the preliminary analysis, it is noted that, though the lateral thrust on the retaining wall in the presence of relief shelves is reduced by 43-48%, use of inappropriate magnitude and distribution of lateral earth pressure in the design calculations might have attributed to the failure of the wall.