This research explored Cape Verdean community advocates' understandings of the structural and social realities that contribute to the increased HIV/AIDS risk of Northeastern U.S.-based immigrant Cape Verdean women. A community perspective informed the analysis of the multi-layered contextual barriers that these advocates identified as limiting the effectiveness of individual-level HIV/AIDS prevention and intervention models. Qualitative content analysis of interviews with nine community advocates revealed several thematic clusters including challenges to (1) perceived institutional and community realities; (2) traditional gender relations; and, (3) traditional ways of thinking. These findings challenge universalist cognitive-behavioral change models of HIV/AIDS prevention and intervention and are critically discussed to better understand the complex realities faced by Cape Verdean immigrant women. A liberatory community psychology perspective framed the research process and contributed to reconceptualizing HIV/AIDS risk as a community problem that requires interventions not simply at the individual and relational levels, but also at the structural level.