In the past two decades, the older prisoner population in the U.S. has experienced unprecedented growth (Carson & Sabol, 2016; Scaggs & Bales, 2016). In fact, older prisoners represent the fastest growing inmate population (Carson & Sabol, 2016). This growth has become an important policy concern for government officials and correctional administrators because these prisoners are substantially more expensive to incarcerate and less likely to reoffend compared to younger prisoners (Chettiar et al., 2012). Older prisoners are more fiscally demanding to correctional systems due to healthcare and special housing considerations (Chettiar et al., 2012; Nowotny et al., 2015; Lemieux, Dyeson, & Castiglione, 2002; Linder & Meyers, 2007; Reimer, 2008). Older prisoners also represent a diverse population comprised of different criminal history profiles. While many prisoners are first time servers in old age, others are chronic offenders who have been in and out of prison multiple times (Beckett, Peternelj-Taylor, & Johnson, 2003). However, there is a void in prior literature regarding differences in the in-prison adaptation and post-prison reentry experiences among these inmates based on being a first time server and alternative definitions of what constitutes being an 'older prisoner. The current study seeks to fill two gaps in the prior literature on older prisoners. First, it will assess how older inmates differ from younger inmates in terms of in-prison adjustment and post-prison outcomes. Previous research studies find that older prisoners are less likely to engage in most types of prison misconduct (Blowers & Blevins, 2015) and to reoffend after prison release relative to their younger counterparts (Durose et al., 2014). What is less documented in prior studies is whether the employment prospects for older ex-convicts differ from those among younger prisoners and the extent to which finding work may, in turn, affect recidivism. Second, this study highlights the heterogeneity that exists among older versus younger inmates in their prison adaptation and reentry outcomes based on age and criminal history. A large percentage of older prisoners have never been previously incarcerated in prison. The Florida Department of Corrections 2013-2014 Annual Report shows that 46.2 percent of prisoners age 50 or older were committed to prison for the first time (Florida Department of Corrections, 2014). Prior research suggests that first time older prisoners may have an especially adverse response, and ultimately adjustment, to their commitment to prison which is manifested through institutional rule violations in the presence of family conflict, suicidal thoughts, depression, and fear of death (Aday, 1994; Leigey, 2015). This study uses data from a release cohort of former prisoners in Florida from 2004 to 2011 to examine differences between younger versus older prisoners. The data include institutional measures, pre-prison employment and criminal histories, and post-prison employment and recidivism information to examine differences in prison adjustment and post-release outcomes among different age groups and being a first time server among older versus younger inmates. By examining the effects of alternative age definitions on three primary outcomes—(1) prison misconduct, (2) post-prison employment, and (3) recidivism—this study contributes to prior literatures on gerontology, prison management, age stratification of post-prison employment opportunities, and recidivism. This study's focus on using old age as a key variable for explaining in-prison and reentry process outcomes is pertinent to a broader study of gerontology because it addresses important issues faced by a special subset of older adults within society. This study also contributes to the current literature on crime over the life course by assessing if and when older inmates are likely to find short-term employment and recidivate.