The main objective of a parole system is to rehabilitate and reintegrate parolees into society. In Malaysia, lack of such community rehabilitation programmes in addition to problems faced by parole officers are a concern. This paper examines the legal and operational predicament faced by the community officers. This paper adopts a qualitative methodology, and data is obtained from five case studies of regional prisons in Malaysia as well as from the Prison Act 1995 and library-based sources. Findings show that rehabilitating parolees is demanding on the parole officers especially so when the rehabilitation purpose and specific duties of such officers are not covered by the Prison Act 1995. Additionally, operational difficulties such as lack of sharing of information on the parolees' rehabilitation assessment and report from the prisons, the officers' lack of expertise and heavy workloads hamper their work.