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This study examines the emergence of specialized courts designed to address misdemeanor and quality-of-life offenses through providing resources and case management in lieu of criminalization. This approach reflects a shift in the criminal justice system, acknowledging the limitations of punitive policies in addressing the root causes of homelessness. These "problem courts" adopt a therapeutic justice model, wherein a collaborative team, including social service providers and a judge, seeks alternatives to the traditional adversarial legal system. Their goal is to disrupt the cycle of arrest and re-arrest commonly experienced by unhoused individuals. Through participant observation and in-depth interviews with officials from community courts in a Southeastern state, this research probes the theoretical foundations and practical outcomes of this evolving system. Findings indicate that while these courts are adept at service provision, they inadvertently sustain tenets of "broken-windows" policing and may incentivize law enforcement to issue more misdemeanor and ordinance violations to ostensibly assist individuals. However, very low completion rates often result in arrest warrants, paradoxically increasing, rather than decreasing, criminalization.