Life after prison can pose challenges for the formerly incarcerated, their families, and wider communities. This research studies Austria where probation services are either mandated by the court or sought voluntarily after prison. Through semi-structured interviews with formerly incarcerated individuals, reintegration experiences from their perspectives are examined. The narratives emphasized social factors that either assuage or complicate life after prison. The main factors addressed were stable housing, the maintaining and (re)building of relationships, and employment. Overall, a lack of stable housing appeared to complicate life after prison the most and also negatively affected relationships and employment. For some, life after prison was further exacerbated by immigration status and a perceived stigma related to the nature of one’s convictions. This study shows the importance of working towards a better understanding of the social context individuals are released into after prison to better meet their individual needs and to counteract recidivism.