This oral history describes three periods of street outreach to injection drug users at risk for HIV in New York City: outreach in an era of public drug markets (1987-1993), outreach in an era of private markets (1993-2006), and network-driven outreach (2006-present). Individual interviews with administrators and supervisors of outreach workers are combined with field notes from the ethnographic research experiences of the first two authors to contextualize, compare, and contrast these distinct periods. The combination and triangulation of these sources of data allow for an analysis of both the specific and the wider social and cultural contexts in which outreach intervention efforts were situated. Through these lenses, the article examines some of the reasons why they were or were not successful and discusses prospects for the future.