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Over many decades, the field of criminology has assessed the experience of incarceration through numerous methodologies. While our understanding of the daily experiences of incarceration and the accompanying pains has advanced, evaluation of how the unique structure, environment, and culture of specific facilities impacts incarcerated individuals remains underexplored. In this research, we utilize in-depth interviews from 88 men incarcerated in a Pennsylvania prison as they discuss their experiences in various correctional facilities. Respondents were asked to compare their incarceration experiences across jails, state prisons, and federal prisons, highlighting distinctive facility-based characteristics they perceived as enhancements or detriments to their time served. Every respondent had experienced incarceration at multiple facilities, some shuffling through dozens of jails and prisons over decades of cyclical incarceration. Through iterative, team-based coding, a number of identified themes illustrate how perceived facility-based cultures, staff competence, racial tensions and dynamics, facility conditions and quality of life factors, and feelings of safety impact incarceration experiences. We discuss the radiating ramifications of these facility characteristics, including the unique position of jails, both in the exceptionally negative views of jail facilities and in the mass exposure to them, given the daily churning of jail populations.