Recent theorisation has pushed stigma research in new directions, arguing for a need to challenge the unequal power relations that impact groups most at risk for HIV-related stigma rather than locate stigma in the individual. Such a conceptualisation resonates with the growing emphasis on structural interventions for HIV prevention that attempt to alter the social context of risk. The paper predominantly relies on longitudinal interviews conducted three times over a 2-year period with sex workers with varying degrees of involvement with the non-governmental organisation (NGO) and community-based organisation. Recognising that stigma is socially constructed and structurally reproduced, the NGO helped mobilise marginalised and hitherto scattered female sex workers to form community-based organisations to challenge their disadvantaged status in society. The authors show how stigma alleviation strategies presented a contradiction: emboldening one group of female sex workers to self-identify as sex workers while making others reluctant to access the intervention-run clinic. The paper builds on a growing body of research that acknowledges the struggles in implementing structural interventions, particularly for NGOs working in regions with a diverse population of sex workers with varying needs. The authors argue that intervention goals of reducing stigma and increasing the use of sexually transmitted infection services do not have to conflict and, in fact, must go hand-in-hand for an implementation to be considered a structural intervention.