Although extensive researches on prison have been carried out, few domestic studies still exist regarding Volunteer Probation Assistants’ (VPAs’) awareness of functions and responsibilities and the problems they encounter alongside Probation and Parole Officers (PPOs) while in the performance of their duties. Thus, this study evaluates the level of awareness of functions among VPAs and the problems encountered by both VPAs and PPOs. This study adopted a quantitative approach, specifically, the descriptive-survey method where only those who were active at the time of this study were chosen. As a result, this study yields that the VPAs understood their tasks; and understood the implications of their work as key indicators of social capital and therapists of behavioral change. By large, the VPAs and PPOs encounter problems on budget, absence of VPAs in the barangays, and long distances travelled by both before reaching the clients’ workplace or residence. Anyhow, the VPAs were capable in coping with the challenges despite financial difficulties they experienced and were able to effectively carry out the tasks they have voluntarily accepted. The PPOs as well, were able to deal with the pressures and stresses because of the commitment of their active supervising VPAs despite their busy hours and the arduous travels to reach the clients.