The Philippines was one of the countries with the highest imprisonment rate for every one hundred thousand people in the population. Based on the relevant data gathered from the World Prison Brief (2020), an increasing trend in the prison population of the country can be observed. In 2016, the total prison population increased to 142,168 with a prison population rate of 140. In 2019, the total prison population ultimately reached 215,000 with a prison population rate of 200. Based on the Mandela rule, prisoners shall be called Person Deprived of Liberty (PDL) who, under the guideline of the United Nations, are entitled to minimum humanitarian treatment. The study employed the qualitative method of research using case study approach. This will be used in describing the reintegration lived experiences of the former PDL in the Iriga City Jail and their coping mechanism on the challenges of their reintegration in the local context. The study employed the qualitative method of research using case study approach. The findings below were revealed in the study. 1. The former PDL experiences anxiety sensitivity on how other people may treat them. They also experienced trust issue from friends and relatives. The PDLs also were seeking for acceptance with fair treatment from the community members. They also expressed some difficulty on having job opportunity. As part of their day-to-day living, their life-long learnings while inside the city jail were somehow instilled to them; and, 2. The results that having the feeling of acceptance from the community, mind shifting, support from the family members, and being hopeful to positive eventualities were very important coping mechanisms in the reintegration process of any former PDL, for them to gain back and boost their self-confidence and live a normal life. The conclusions below were drawn in the study. 1. There were shared lived experiences of the former PDLs in the reintegration process which notably highlights their anxiety sensitivity, seeking for fair treatment from the community members, the difficulty on having job opportunity, and the life-long learnings instilled to them while inside the city jail. 2. Having the feeling of acceptance from the community, mind shifting, support from the family members, and being hopeful to positive eventualities were very important coping mechanisms in the reintegration process of any former PDL, for them to gain back and boost their self-confidence and live a normal life.