The emergence of tertiary desistance underscores the need to go beyond the current focus on behavioral and identity/cognitive transformation in desistance research and take into account the social context that impacts desisters. This study aims to explore the experiences of people with a criminal history during the tertiary desistance phase by conducting a qualitative metasynthesis. We conducted literature searches across seven databases in January 2023: CINAHL, MEDLINE, ProQuest, PubMed, PsychINFO, Scopus, and Web of Science. After screening and assessing the quality of identified qualitative studies on tertiary desistance, we selected 13 relevant studies. Our synthesis indicates that desisters commonly encounter numerous challenges due to the stigma associated with their past criminal activities, which may result in feelings of insecurity, a negative self-image, and a reluctance to socialize with others. However, once desisters are recognized and trusted by significant others and society, they utilize the recognition and trust to overcome the stigma and experience a positive change in their sense of belonging. Given that tertiary desistance is an interactive process involving both people with a criminal history and society, it falls upon society to afford them a second chance at rehabilitation and reintegration.