Health providers can play an important role in communication about pregnancy, particularly for women at increased risk for pregnancy complications, including female sex workers (FSWs) living with HIV. This study explored factors related to patient-provider communication about pregnancy among 253 FSWs living with HIV of reproductive age in Santo Domingo, Dominican Republic. A cross-sectional design was employed including structured socio-behavioral surveys. Data were analyzed utilizing bivariate and multivariate logistic regression. Of the 253 FSWs living with HIV in this study, 95.7% had been pregnant at least once (median: 4; IQR: 3,6), 28.0% wanted more children and 36% reported a pregnancy after HIV diagnosis. Over half of participants (58.0%) reported having ever spoken to a health provider about pregnancy while living with HIV. Multivariate logistic regression found significant associations between having spoken to a health provider about HIV in pregnancy and a more positive perception of their provider (AOR: 2.0; 95% CI: 1.0, 2.5) and years since HIV diagnosis (AOR: 1.1; 95% CI: 1.0, 1.1). Participants were less likely to speak with a provider if they had a history of drug use (AOR: 0.4; 95% CI: 0.2, 0.9) or current alcohol use (AOR: 0.5; 95% CI: 0.3, 0.9). Findings highlight the importance of non-judgmental and tailored provider-initiated conversations surrounding pregnancy. Future research is needed to better understand how and when pregnancy communication is initiated, as well as the content of clinical care conversations, to address the reproductive health of FSWs living with HIV.