||ABSTRACT. The politics of crime and punishment generally pushes Governments to adopt harsher measures to ﬁght crime, yet there is a movement in Singapore toward a softer approach in some areas. Singapore has a robust – many would say tough – criminal justice system, for some aspects of which it has and will continue to receive international criticism. Less known is the fact that it has recently invested in more holistic and compassionate strategies, through criminal diversion programs and community sentencing. This article explains this shift in the context of signiﬁcant social and political changes taking place in Singapore, heralding a more liberal society and open Government. The paper also engages with some of the theoretical and philosophical arguments in favor of criminal diversion and provides a brief overview of the recent diversionary programs in Singapore.