This study is on the social adaptation of inmates after their discharge from prison and such a study on the social adaption is critical for preventing second conviction after inmates’ discharge from prison and for ensuring that they can become viable members of their respective societies. This study was carried out targeting six inmates who are confined to the XX Prison located in Gyeonggi Province by administering in-depth interviews. To carry out analysis of the qualitative contents, inmates’ experience with crime, their relationships with their family members, their experience in the prison, and the set of supports needed for social adaptation were analyzed in-depth. The analysis results demonstrate that the inmates face hardship during the time of confinement due to the severance of the ties with the outside environment and their family relations. Some of them experience family dismantling. This severance with their family and the environment negatively affect social adaptation of inmates after discharge from prison. Family is the most important support system after the discharge, and it is very important in the sense that it serves as the link to the outside environment. There are many instances in which inmates participate in religious programs while confined while not many participated in the program that exert significant influence on their social adaption such as occupational training program. Moreover, inmates fear social stigma, lack of employment opportunity and the challenge of having to maintain their work life after getting discharged. Accordingly, this study capitalized on the results of the study to present the direction for the social services and policies to ensure effective social adaptation of inmates after discharge from prison. Moreover, the study highlighted the need to adopt corrective social welfare worker system to provide comprehensive set of services to ensure inmates’ adaptation in the prison and after their discharge to prevent dismantling of inmates’ families and to develop programs in the prisons to help maintain sense of affinity with family members, counseling program so that the inmates can sustain link with the outside environment and occupational training program.