Over the last several decades, proactive policing, in which departments use data on reported crimes to determine where local police officers will target their surveillance, has increased police contact with residents in certain neighborhoods. Drawing on field research conducted over a three-year period (2007-2010) among adult and adolescent African American men in a San Francisco neighborhood with a concentrated poor, Black population, I provide an ethnographic account of routine encounters with the police that structure adolescent boys' daily lives in potentially significant ways. I build on Erving Goffman's discussion of "patterns of mortification" to describe how typical encounters unfold in the day-to-day lives of young men and consider the implications of such encounters for healthy adolescent development.