Cisgender female sex workers (CFSW) continue to face structural barriers to HIV prevention. We analyzed the acceptability of the oral HIV self-test (HIV-ST) among CFSW as part of a pragmatic trial on HIV prevention in Brazil. Data from in-depth interviews conducted with 12 women from diverse sex worker contexts and participant observation were analyzed using thematic analysis. CFSW valued autonomy in their workplaces and saw the HIV-ST as a possibility for self-care. Some feared clients’ reactions, manager reprimands, and a positive result. HIV and sex work stigma largely drove self-care practices and perceived acceptability of the self-test. We argue that the autonomy offered by the self-test presents a paradox: increasing autonomy on the one hand while risking sidestepping structural dimensions of HIV vulnerability on the other. These nuances must be considered in interventions promoting the HIV-ST by considering the specificities of sex worker contexts, addressing stigma, and effectively involving CFSW and their organizations in intervention development.