In grappling with mass incarceration, many policymakers attempt to intervene during reentry, or the process of leaving jail or prison and “reentering” the community. Some of the more obvious reentry challenges include removal from welfare programs as a result of convictions, despite the fact that welfare programs can be beneficial for reentry. Because state and federal statutes create lifetime bans on welfare programs for people with convictions, policymakers focus on removing these bans. However, it is possible that barriers to public assistance exist regardless of having a conviction, evidenced by examining the pretrial population. These people leave jail without convictions, but are still often unequipped for what waits for them after hours, days, or months of being away from their lives due to pretrial detention. The pretrial population has been ignored in conversations about removal from or limited access to welfare programs during reentry. Because of that, I hope to highlight how pretrial detention affects this access through a case study on Cook County Jail. The bulk of my research comes from interviews with forty-one individuals, including bureaucrats from Cook County Jail jail and relevant welfare agencies, and people working with formerly incarcerated individuals at nonprofits and advocacy organizations. Overall, I find that pretrial detention produces formal and informal barriers for people trying to enroll in or maintain their enrollment in Medicaid, SNAP, and SSI upon release from Cook County Jail. Formal barriers are triggered by statutes and jail procedures, while informal barriers directly result from bureaucracy and on-the-ground practices. I ultimately recommend legislative action and the implementation of programmatic interventions at the jail. If the jail wants to facilitate better outcomes upon release and lower the likelihood of a return to jail, it has to be committed to combating these barriers produced by pretrial detention.