Population health programs often rely on broad categories to guide HIV service delivery for key populations, but these classifications can hide important social differences that influence engagement in care and trust in health systems. Using cross-sectional data from 150 transgender individuals living with HIV in Mumbai and New Delhi, we identified distinct social position profiles based on self-reported gender identity, sexual orientation, education, and livelihood. Three groups emerged: (1) educated transgender women engaged in sex work, (2) heterosexual transfeminine individuals with limited education engaged in sex work, and (3) Hijra and related identities and LGBQ+ individuals involved in dual livelihoods of sex work and begging. Membership in Class 3 was associated with significantly lower odds of achieving optimal ART adherence compared with Class 1, after adjusting for age and city. These findings emphasize that broad population categories used in HIV programs can hide high-risk subgroups and limit the success of adherence interventions. The study advocates rethinking differentiated service delivery models to better reflect the lived realities and social positions marginalized communities face, with the aim of improving both equity and program effectiveness in HIV care and other chronic disease services.