A growing area of concern among prison reform advocates and human rights activists is the “greying prison population” or the continuous, unified growth in the number of older incarcerated individuals. Older individuals experience an accelerated aging process while incarcerated, but are less likely to reoffend upon release. While the aging prison population has in recent years become a focus of criminological and gerontological scholars, the lived experience of older formerly incarcerated individuals during the reentry process remains understudied. Using a qualitative approach, this cohort study seeks to further elucidate the unique needs, beliefs, and perceptions of this population within the context of an unprecedented public health crisis, the COVID-19 pandemic. A series of interviews was conducted with participants in a comprehensive reentry program for formerly incarcerated older adults in New York City who had been released between 2019 and 2020. Participants (n = 9) reported that their greatest challenges during the reentry process were securing safe and stable housing, managing physical and mental health issues, and coping with trauma, social isolation, and interpersonal conflicts. Other criminogenic factors which are typically associated with recidivism were less frequently reported among the cohort, including challenges securing employment and substance abuse issues.