The aging prison population encompasses the fastest rising age category in the US prison system and are continuing to receive national focus due to its high economic and social costs. Due to their confinement status, the aging incarcerated individuals are subject to insufficient health care and risky lifestyles and behaviors. This leads to an even more rapid progression of these concerns than commonly found in typical aging populations. Due to this, correctional departments are challenged to provide the necessary care and support. This study reviewed snapshots of 1998, 2008, and 2018 incarcerated population data from a mid-sized correctional department in efforts to evaluate the trends of the aging incarcerated population (ages 55 or older) over the past two decades. The findings highlight: a) The prevalence of the aging incarcerated population and the change in populations over the past two decades; b) The similarities and differences between the aging and non-aging incarcerated populations; c) The factors that distinguish the 1998, 2008, and 2018 aging incarcerated population; and d) The recidivism and violation rates of the 1998, 2008, and 2018 incarcerated population. This endeavor helped gain insight and knowledge into the impact of the aging incarcerated population. Studies like this one benefit in providing consideration to policy changes focusing on the geriatric population, attention to the aging population’s physical and mental health, and evaluation of new programs that can positively impact the aging incarcerated population.