A growing literature examines the extent to which the criminal justice system perpetuates poverty and inequality. This research examines how anti-homeless laws produce various forms of police interactions that fall short of arrest, yet have wide-ranging impacts on the urban poor. Our analysis draws on a citywide survey of currently and recently homeless people, along with 43 in-depth interviews, to examine and reveal the mechanisms through which consistent punitive interactions, including move-along orders, citations, and destruction of property, systematically limit homeless people’s access to services, housing, and jobs, while damaging their health, safety, and well-being. Our findings also suggest that anti-homeless laws and enforcement fail to reduce urban disorder, but create instead a spatial churn in which homeless people circulate between neighborhoods and police jurisdictions rather than leaving public space. We argue that these laws and their enforcement, which affected the majority of study participants, constitute a larger process of pervasive penality—consistent punitive interactions with state officials that rarely result in arrest, but that do material and psychological harm. This process not only reproduces homelessness, but also deepens racial, gender, and health inequalities among the urban poor.