This dissertation engages a fundamental concern for sociologists, criminologists, and scholars of urban poverty: how authorities attempt to better control marginal social groups, and how those populations counteract and even resist these efforts. Drawing on five years of ethnographic fieldwork, interviews, and archival research, the dissertation analyzes daily life on the streets of Los Angeles' Skid Row district, a neighborhood widely-regarded as the "homeless capital of America," distinguished as containing what is arguably the largest concentration of standing police forces found anywhere in the country, if not the world. Tracing the historical trajectory of neighborhood development into current-day, street-level interactions between police officers and Skid Row's impoverished and homeless inhabitants, I argue that a new model of social control has emerged, tightly wedding rehabilitative and punitive interventions - what I term "therapeutic policing." Examining inhabitants' everyday experiences of Skid Row in the shadow of policing, the text further examines a range of strategies - from quiet subversion to overt opposition - by which those in the neighborhood attempt to resist the mandates of therapeutic policing. Throughout the analysis, I demonstrate that the increasing omnipresence of surveillance, detainments, and arrests in Skid Row, and other marginalized and stigmatized urban neighborhoods, is fundamentally reshaping the manner in which residents come to understand themselves, their peers, and their communities.