HIV remains a central reproductive health concern, particularly in regions where stigma and structural inequities undermine access to healthcare. Young transgender women and sexually diverse men in Jamaica face disproportionate HIV risk due to overlapping vulnerabilities including poverty, criminalisation, and social discrimination. This paper examines the intersection of stigma, HIV vulnerability, and reproductive health outcomes within this population. By integrating qualitative insights with reproductive medicine frameworks, we highlight how structural barriers influence access to contraception, fertility planning, pregnancy-related care, and prevention of mother-to-child transmission (PMTCT). Policy reforms and targeted interventions are proposed to reduce inequities and improve reproductive health outcomes for marginalised groups.