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Misdemeanors comprise the vast majority of police-citizen encounters and cases processed in criminal court, relative to more serious, felony-level offenses. The complexities of misdemeanors–particularly from the perspectives of the police officers who enforce such laws and the judges, prosecutors, and defense attorneys who manage misdemeanor case processing–have received relatively little scholarly attention. We draw on in-depth interviews with retired NYPD officers and New York City court officials to more fully understand how misdemeanor enforcement and case processing has changed over time and how front-line police and court workers have experienced such changes. Findings from interviews with police officers shed light on how officers understand and experience proactive policing tactics and the pressures associated with data-driven accountability. Interviews with court officials reveal shared concerns over the perceived “worth” of some charges in the era of “quality-of-life” policing and the ongoing challenges of managing high misdemeanor case volumes, as well as an awareness of the direct and collateral consequences of misdemeanor enforcement activity and the various strategies used by court actors to mediate those consequences. The implications of this research for police-community relations, due process, and procedural justice are explored.