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Research has demonstrated that there are racial differences in the outcomes of defendants who participate in problem solving courts. Defendants of color are less likely to succeed and complete program mandates in problem solving court programs. Most of the research to-date on problem solving courts has been quantitative and are limited in their exploration of these inequalities. It is well known that judicial involvement is critical in the process of most problem solving courts. This paper seeks to understand how these racial differences occur by qualitatively examining two judges in community courts located in the northeast region of the U.S: one white male and one black female. The judges’ interactions with defendants and the ways they address race and racial dynamics in their courtroom are explored through daily field observations and interviews within a two-month period. Findings indicate that the racial makeup of the judge does play a role when addressing race in community court programming and can influence how rapport is built between defendants and judges. Furthermore, other actors in the courtroom workgroup, such as attorneys, highlight their experiences with race in a court setting. Future research suggestions and policy implications are addressed.