Chapter seven explores the initial impacts of re-entering a world these lifers left many years ago. The chapter highlights specific roadblocks to re-entry. These include the ‘felon label’, the implications stigma, labeling, and the widespread availability of criminal background checks. These factors prevent lifers from obtaining housing and employment. The chapter discusses how interviewees managed the stigma of being an ex-offender. Deriving indicators from life-course theories, the chapter further details how relationships with family, intimate partners and children influenced the interviewees over the years. By being in prison for decades, these lifers have been removed from structures that favor maturation and provide sources of informal social control, such as employment, intimate relationships, family relationships and parenthood. Prison, in this view, has disrupted their journey of going straight.