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A cohort of frequently incarcerated individuals in the New York City jail system was identified through "hot spotting" analysis. This group demonstrated higher levels of substance use, mental illness, and homelessness than the general jail population, and was typically incarcerated on minor criminal charges. To understand this population better, in-depth interviews (n = 20) were conducted at three Rikers Island correctional facilities with people who had entered the jail system at least 18 times in a six-year period. Findings showed that life circumstances, chronic homelessness, mental illness, and substance use resulted in repeated institutionalization across multiple settings. Participants described an "institutional circuit" that promoted a state of permanent instability characterized by rotating involvement with custodial institutions. Exiting the institutional circuit requires the ability to navigate complex bureaucratic systems; however, without structural reorganization in social service delivery and an emphasis on permanent housing, participants in this group are unlikely to break the cycle.