Female sex workers (FSWs) living with HIV are a vulnerable population for multiple health concerns and have been vastly understudied in public health literature. This study analyzes factors related to pregnancy among 268 FSWs living with HIV in the Dominican Republic. Results indicate that 34 % of participants had been pregnant since HIV diagnosis. Multivariate analysis revealed significant associations between pregnancy after HIV diagnosis and ART interruption (AOR 2.41; 95 % CI 1.19, 4.94), knowledge of mother-to-child transmission (AOR 2.12; 95 % CI 0.99, 4.55), serostatus disclosure to a sex partner (AOR 2.46; 95 % CI 1.31, 4.62), older age (AOR 0.91; 95 % CI 0.87, 0.95) and a more negative perception of their health provider (AOR 0.56; 95 % CI 0.34, 0.93). Results indicate noteworthy associations between having been pregnant and the health provider experience and ART interruption, indicating a significant need for further research on this population to ensure both maternal and child health.