According to the 'Consolidated Guidelines on HIV Prevention, Diagnosis, Treatment and Care for Key Populations' there are five groups of people at elevated risk of HIV, including 'transgender women or transgender men who have receptive anal sex with men'. Although cost effectiveness strategies and best practice lessons recommend targeting specific populations for HIV prevention, existing risk categories lack specificity, and may in fact cause further confusion. Existing categories of risk often perpetuate notions of gender and sexuality that can erroneously exclude, alienate, and stigmatise those who are at the highest risk and thus should be prioritised. We review the troubled history of the MSM category and the problematic conflation of trans feminine individuals and MSM in much of the existing HIV literature, and how this practice has stymied progress in slowing the HIV epidemic in the most at-risk groups, including those who do not fit neatly into binary notions of gender and sex. We draw from examples in the field, specifically among trans feminine people in Beirut and San~Francisco, to illustrate the lived experiences of individuals whose identities may not fit into Euro-Atlantic constructs of HIV prevention categories.