The number of people reentering society after imprisonment has increased dramatically in recent decades in direct correlation with the growing prison population. As a result, empirical studies of prisoner reentry have also increased, but these studies typically focus on large urban areas and use quantitative methodologies. The current study expands the existing literature by examining qualitatively the reentry experiences of 43 male offenders living in a small metropolitan community. Participants were interviewed at the 3-month mark of their release from prison. They were asked about the strains and obstacles they encountered at three distinct time periods since their release: the first days of release, the 1-month mark, and the 3-month mark. These former prison inmates were also asked to identify any program or service that had helped or could help their reintegration into society. The results suggest that core obstacles and strains in reentry, such as issues with money, employment, and reconnecting with family, are consistent across geographical location. The study also produced some unique findings, such as psychosocial challenges being cited most frequently as obstacles or strains, the role of employment beyond its financial importance, and the negative aspects of religious components in reentry programs. Several policy recommendations relevant to the findings are discussed. (Published Abstract)