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Globally, social inequalities contribute to elevated sexually transmitted infections (STIs) rates among transgender women. High syphilis prevalence has been documented among transgender women in Latin America. Little is known, however, of syphilis testing uptake among transgender women in Jamaica, where homosexuality is criminalized. The study objective was to understand factors associated with opting-in for syphilis testing and a syphilis infection history among transgender women in Jamaica.We conducted a cross-sectional tablet-based survey of 137 transgender women between March and November 2015 in Jamaica. Bivariate analyses were used to assess differences across sociodemographic, intrapersonal, interpersonal, and structural factors based on syphilis infection history. We conducted univariable and multivariable logistic regression to determine the odds ratio for opting-in for syphilis testing for all factors associated with testing uptake at a P value of less than 0.05 in bivariate analyses, controlling for sociodemographic characteristics.Among 137 participants, 83 (60.6%) opted in for syphilis screening and 8 (9.6%) had positive rapid test results. One quarter of participants (n = 26; 25.2%) reported being HIV positive. Opting-in for syphilis testing was associated with the following: 1 health (HIV-positive serostatus: adjusted odds ratio [AOR], 4.33; 95% confidence interval [CI], 1.31–14.26), 1 intrapersonal (perceived STI risk: AOR, 1.58; 95% CI, 1.04–2.40), 1 interpersonal (childhood sexual abuse: AOR, 2.80; 95% CI, 1.03–7.62), and 1 structural (incarceration: AOR, 0.27; 95% CI, 0.11–0.71) factor.This study identified factors (HIV-positive serostatus, perceived STI risk, childhood sexual abuse, no incarceration history) associated with syphilis testing uptake among transgender women. Findings can inform multilevel STI testing, prevention, and care strategies tailored for transgender women in Jamaica.