Based on my 7 months of ethnographic research with “flying” or mobile female sex workers (FSWs) in the eastern metropolitan city of Kolkata, India, I argue that the human immunodeficiency virus (HIV) prevention programs have a limited outreach and impact within the community because of the fundamental differences in how the nongovernmental organizations (NGOs) staff and flying FSWs perceive the risk of HIV. This article examines flying FSWs perceptions of HIV risk and the NGOs sexual health outreach services. Further, the implications for HIV prevention programs and social work practice are discussed.