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Pretrial populations have high rates of behavioral health and physical health problems, many of which remain unaddressed (both in jail and during pretrial release) due to limited access to services. Local jurisdictions have developed pretrial services agencies to supervise defendants during the pretrial period, but these agencies focus primarily on monitoring rather than service connection. Although qualitative research on the lived experiences of pretrial defendants can inform our understandings of these individuals’ needs, few studies have examined pretrial defendants’ perceptions of their own physical and behavioral health challenges and their views on the role of pretrial services in treatment connection. We conducted semi-structured interviews with 75 defendants on pretrial supervision across 10 counties to explore how participants described both physical and behavioral health challenges during their time in pretrial detention and on release. We found that health problems disrupted participants’ stability in the community, and that these health challenges were often in turn compounded by stressors related to the death of loved ones, interpersonal conflict, employment difficulties, and pretrial processing. Together, these findings underscore the complex interplay between health problems and pretrial defendants’ community stability. We discuss how this dynamic poses challenges for directing individuals to needed services and supports.