Section 1 outlines the legislative provisions governing the community-based supervision and treatment of offenders. The Probation of Offenders Act governs probation practices in Singapore, while the Children & Young Persons Act (CYPA) governs the criminal justice response to juvenile offenders. Probation practices are outlined, including the conditions under which probation orders may be made and the requirements of the probationer. Singapore’s probationary practices involve a tiered supervision system in which periods of probation range from 6 months to 3 years. Community Service Orders (CSO) were introduced as a condition of probation in 1996; they require an offender to perform unpaid work for a specified number of hours. Singapore’s probation system includes core and elective programs, focused programs designed to target specific risks, probation services in family service centers, and employment development programs. Since approximately 75 percent of Singapore’s probation population is below the age of 18, probationary services focus on the family as the main agent of positive change and the basic building block of society. Singapore’s probation services also engage the community in the rehabilitation of young offenders and usually have over 300 active volunteer probation officers. Section 2 discusses future challenges facing the probation system in Singapore. Rising unemployment rates are expected to strain the resources of the rehabilitation programs. Partnerships that encourage collaborative research on criminal justice best practices are recommended for Singapore to remain abreast of current knowledge. Appendix