Exponential growth in order maintenance policing and associated misdemeanor sanctions have led to disproportionate consequences for people of color. Using data from qualitative interviews with individuals in the metropolitan St. Louis, Missouri, region, the current study documents the racialized and monetized nature of police contact. This work extends extant scholarship by considering how minor contact with the police shapes individual avoidance behaviors and activity spaces, places where people work and live. We consider how the combination of monetary sanctions, warrants, incarceration, and overpolicing in the region affects avoidance behaviors, particularly for people of color. Our findings suggest that the frequently unpredictable nature of police contacts and the parochial and often profit-focused structure of policing organizations in the region leads individuals to modify the ways in which they move through the region and, for some, to isolate. Narratives reflect the need for constant calibration of behaviors and decisions, as well as the legacy that police contact and monetary sanctions can have on everyday routines.