DescriptionYoung adult offenders face significant challenges to successful reintegration including stigma, obtaining employment, neighborhood and community influences, family and peer relationships, educational deficits and developmental challenges. While these factors, integral in the reentry process, have been explored in existing literature, less is known about the reentry experiences of young adult offenders experiencing both the transition from jail to the community and from adolescence to adulthood. Utilizing qualitative methods to obtain thorough narratives of these experiences, this dissertation examines how 18-24 year-old offenders balance the experiences of jail with the reintegration and developmental challenges facing this population upon their release. Specifically, this study explores labor market and neighborhood experiences following the release from jail to better understand how these individuals balance both negative and positive social capital within their communities. In this study, I conducted both pre-release and post-release interviews with 19 young adult male offenders. Participants were initially interviewed within three months of their release and participated in follow-up interviews within four to eight months following their release. It was my expectation that the jail experience would decrease positive social capital in the labor market and increase negative social capital in participants’ neighborhoods. Findings in this dissertation found that while some participants experienced a slight increase in social reputation among criminally active peers, the expectation that incarceration would enhance criminal enterprise was not supported. However, the loss of positive social capital was found within the labor market and some participants reported experiencing a “balancing act” which consisted of maneuvering between both positive and negative social capital opportunities. Findings also show how reentry experiences are often shaped by the developmental processes characteristic of young adult offenders entering into adulthood. This dissertation addressed the gaps in empirical literature by exploring why incarceration has ambiguous effects on different types of offenders. By closely examining a specific offending population, this study contributes to criminological theory by expanding our knowledge of the heterogeneity of incarceration experiences and the deterrent effects, if any, the jail experience has on young adult offenders.