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Background: Effective treatment has extended the life expectancy and reduced disability in people living with HIV (PLWH). However, previous research has found 45–65% of working-age PLWH were unemployed compared to 5–10% in the general public of North America and Europe. We examined the barriers to gaining employment among PLWH. Methods: Thirty-five in-depth interviews were conducted in person or over the phone with PLWH living in Toronto or Ottawa. This included PLWH who were unemployed but actively seeking employment, as well as PLWH who had successfully gained employment through an agency that specifically supported PLWH funded by the AIDS Committee of Toronto. Interviews were conducted between February 2019 and March 2020. All interviews were audio-recorded, transcribed and analyzed using thematic analysis. Results: The majority of participants were between the ages of 40–55 and identified as male. Participants shared many common barriers when describing their attempts to attain or maintain employment. Although varying in employment status at the time of the study, consistent barriers included experiencing HIV stigma in workplaces, challenges overcoming mental health illnesses, and difficulties in navigating social assistance and unemployment insurance programs when pursuing a return to work. Conclusions: PLWH face significant barriers when attempting to engage with employment opportunities. Health providers and organizations can do more to support campaigns to end HIV stigma, to support individuals in pursuing employment, and to advocate for policy change that supports reentry into the workforce for PLHA. [ABSTRACT FROM AUTHOR]