Kleptomania is an enigmatic condition and is among the very few psychiatric disorders in which crime is medicalised and used as a legal defence. The scientific literature on kleptomania is scarce. Early literature and recent studies have shown a female preponderance, with an early age of onset of stealing in people with comorbid personality disorder(s). In a retrospective review of the case notes of theft offenders who had forensic psychiatric evaluations performed in a one-year period in 2010 at the Institute of Mental Health, Singapore, we found three patients who were diagnosed with kleptomania. In this report, we describe the pertinent clinical and sociodemographic characteristics, as well as the diagnostic issues of kleptomania in relation to the three cases.