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Gay, bisexual and queer men in Singapore are disproportionately represented in prevalent HIV infections, relative to the general population. While anticipated stigma has been found to be a barrier to HIV/STI testing among gay, bisexual and queer men, little effort has been made to contextualise such stigma within the broader sociocultural milieu. We conducted 35 in-depth interviews with a purposively recruited sample of men in Singapore with a focus on topics such as sexual identity development, formative sexual experiences and HIV/STI testing experience. Interviews were analysed through thematic analysis using techniques borrowed from a grounded theory approach. Participants drew on their past interactions with family, friends, religion, the gay, bisexual and queer men's community and the wider society to construct meanings of deviance in the context of their sexuality. Participants articulated how anticipated stigma was rooted in such deviance, and how clinics or other HIV/STI-related health services served as physical spaces of costly disclosure by exposing or imposing 'deviant' identities on individuals who access these physical spaces, which were otherwise concealed. Findings from the study provide a framework for actions and interventions to address the roots of anticipated stigma in the context of HIV/STI testing among gay, bisexual and queer men.