Background Structural stigma and institutionalised discrimination towards people living with HIV remain pervasive in many settings. However, qualitative explorations of experiences of stigma, health and social service engagement, and quality of life among people living with HIV in Singapore remain under-researched. Methods Semi-structured interviews were conducted with 73 participants in Singapore. These included 56 people living with HIV (30 men who have sex with men, 23 heterosexual men, and 3 women) and 17 stakeholders including healthcare professionals and other allied workers. Interviews focused on participant perspectives or experiences of HIV diagnosis, navigating healthcare, attitudes towards HIV, and impact of HIV on relationships. Data were analysed through inductive thematic analysis. Results Our findings were framed within a minority stress model, highlighting the distal and proximal stressors relating to living with HIV. With regard to distal stressors, participants highlighted that they had experienced or were aware of institutionalised discrimination towards people living with HIV across various aspects of their lives. These included experiences - overt and covert - of discrimination in education, workplace, and healthcare settings. With regard to proximal stressors, participants highlighted the role of anticipated stigma and the stress of concealment. This included participants' fear of potential legal and/or social repercussions resulting from the disclosure of their HIV status, actions that they may not be able to anticipate and articulate. Although employers may not overtly discriminate, the fear of such anticipated discrimination influenced decisions to conceal HIV status in job applications and workplaces. This restricted agency for the people living with HIV in our study by affecting their regular medical follow-ups, socialising behaviours, and overall quality of life. Consequently, many participants felt that concealment of their status, and forgoing potential educational, employment, and even health opportunities, were the only ways of protecting themselves from such forms of stigma and discrimination. Conclusions This study found that anticipated stigma and discrimination diminished the quality of life of people living with HIV in Singapore. Implementing an anti-discrimination framework could address the unpredictability and alleviate the manifold unknowns of anticipated stigma.