Despite concerted prevention efforts, young South African women remain at the epicenter of the HIV epidemic. Although these women have grown up in a community powerfully affected by HIV, systematic investigation into how this “second generation” of HIV-affected youth navigates HIV risk is lacking. This study qualitatively explored a complex interplay of factors influencing HIV risk among young pregnant women in KwaZulu-Natal, South Africa. We conducted in-depth interviews with 35 pregnant women (22 HIV-uninfected and 13 HIV-infected) aged 18–21, 18 healthcare providers, and focus groups with 19 community stakeholders. Among the young women, HIV knowledge was high, and many reported taking some action to prevent pregnancy or HIV; however, these efforts were not routinely implemented. Themes related to HIV acquisition risk from all participants were organized using a socioecological framework and revolved around individual and developmental experiences (personal experience with HIV, perceived invincibility), family barriers (lack of adult supervision, pressure to leave school), relational barriers (lack of disclosure and partner communication, “burn out” around attempts to discuss condom use with partners, overdependence on partners), community-level barriers (township environment, lack of structured activities), and social barriers (poverty, HIV-related stigma). Some novel concepts emerged from the data, including an understanding of how overdependence on the romantic relationship may develop. Current HIV prevention efforts, including traditional HIV counseling and testing, condom distribution, and biomedical agents for HIV prevention, are unlikely to be effective without a broader, ecological up-to-date understanding of the evolving, intertwined, and complex constellation of factors that drive HIV risk behavior in this high-risk population.