Transgender women are overrepresented in the Caribbean HIV epidemic. The study objective was to examine correlates of HIV infection and HIV testing among transgender women in Jamaica. We implemented a crosssectional survey with transgender women in Kingston and Ocho Rios, Jamaica. We conducted multivariable logistic regression to identify factors associated with HIV testing and HIV infection. Among 137 transgender women [mean age 24.0; standard deviation (SD) 5.5], three-quarters (n = 103, 75.7%) had received an HIV test. Of these, one-quarter (n = 26, 25.2%) were HIV positive. In multivariable analyses, HIV testing was associated with: perceived HIV risk [adjusted odds ratio (AOR) 2.42, confidence interval (CI) 1.36–4.28], depression (AOR 1.34, CI 1.01–1.77), forced sex (AOR 3.83, CI 1.42–10.35), physical abuse (AOR 4.11, CI 1.44–11.72), perceived transgender stigma (AOR 1.23, 1.06–1.42), having a healthcare provider (AOR 5.89, CI 1.46–23.77), and lower HIV-related stigma (AOR 0.96, CI 0.92–0.99), incarceration (AOR 0.28, CI 0.10–0.78), and drug use (AOR 0.74, CI 0.58–0.95). HIV infection was associated with the following: homelessness (AOR 5.94, CI 1.27–27.74), perceived HIV risk (AOR 1.67, CI 1.02–2.72), depression (AOR 1.39, CI 1.06–1.82), STI history (AOR 56.79, CI 5.12–630.33), perceived (AOR 1.26, CI 1.06–1.51) and enacted (AOR 1.16, CI 1.04–1.29) transgender stigma, forced sex (AOR 4.14, CI 1.49–11.51), physical abuse (AOR 3.75, CI 1.39–10.12), and lower self-rated health (AOR 0.55, CI 0.30–0.98) and social support (AOR 0.79, CI 0.64–0.97). Transgender women in Jamaica experience high HIV infection rates and suboptimal HIV testing. Combination HIV prevention approaches should address transgender women's social and structural vulnerabilities.