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Homelessness is a multifaceted issue involving problems related to mental health, substance abuse, and trauma. Despite its multifaceted nature, homelessness has been criminalized and oftentimes dealt with through the police and criminal justice system. Researchers have recently pushed for non-arrest approaches to homelessness in hopes of creating more long-term solutions. The current case study explores the approach of the Indio Police Department’s (IPD) Community Outreach Resource Program (CORP). CORP is a collaborative, non-arrest approach to homelessness, where individuals experiencing homelessness and participating in service provider programming are recommended to CORP stakeholders for the removal of accrued fines/fees at the end of their programming. We draw on focus groups with criminal justice and service provider stakeholders, interviews and surveys with CORP participants, and IPD ride-alongs to understand experiences with this approach. The results suggest that collaborative approaches to homelessness are promising because they combine the efforts of different stakeholders, generating a multifaceted approach to a multifaceted problem. Concerns do still exist, however, related to the long-term impact of these programs when they are not coupled with subsequent aftercare.