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 cross-sectional 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.