Probation has been in existence in Singapore for more than 70 years. Given its long existence and vested interest in community-based sentencing, this paper calls for an effective measurement of probation officers training and supervision of the offenders measured against recidivism. First the paper focuses on the genesis and evolution of probation coupled with a brief description of programs conducted by probation officers since its introduction till its present iteration, along with its merits. The emphasis lies in the shift from a supervisory program to one which proactively seeks to transform behaviour, hence reaffirming remodelling character of probation. Second, it is recommended that effectiveness of training, supervision of offenders by Probation Officers be measured against the rate of recidivism. To this end, it is proposed that effectiveness of probation can only be measured against recidivism given that probation targets criminogenic needs of offenders. An evaluation of data presented on recidivism suggests that while the recidivism rate is decreasing, it does not maximize the potential role of Probation Officers. Third, training along the lines of Strategic Training Initiative in Community Supervision (STICs) program can be considered to enhance lower recidivism rates. Lastly, it is recommended that Randomized Controlled Trials (RCTs) be conducted for evidence-based policy making in criminal justice system, since RCTs can be useful in assessing the efficacy of probation as a community-based sentencing tool, particularly whether the policy orientation of probation meets the goal of reducing crime.