Offender populations have various types of disabilities that may be visible or invisible, cognitive, emotional or psychiatric, sensory, physical or mobility related, or any combination of disabilities and chronic conditions, as well as those that are undiagnosed. The presence of a conviction or offender record adds a dimension that creates roadblocks to community reintegration and employment, which is often magnified in rural settings. Often, ex-offenders lack sufficient human and social capital to help them navigate many life challenges outside of prison. Furthermore, ex-offenders are burdened by exclusionary and stigmatizing effects of restrictions on civic and family participation. The purpose of this chapter is to discuss the stigma of having an (ex)-offender status in rural communities and how the presence of such a status in conjunction with disability may hinder further vocational rehabilitation outcomes. Information is presented on statistics of offender populations, employment barriers, employers’ attitudes and practices in the hiring of ex-offenders, and the confluence of rural settings on community reintegration and employment of ex-offenders. In addition, strategies for post-incarceration release transition planning and vocational rehabilitation (VR) services are presented. Although inmates can serve their time in different types of correctional facilities (e.g., jail, state prison, federal prison), this chapter focuses mainly on ex-offenders within prison settings.