We sought to determine: (1) the perinatal outcomes in the subsequent pregnancy; (2) the natural history of serologic titers over the course of the two pregnancies; and (3) the incidence and risk factors for delivering an infant with congenital syphilis in the subsequent pregnancy. Over a five-year period, we reviewed the charts of 46 women with maternal syphilis during pregnancy who had a subsequent pregnancy and delivered in our institution. The initial and subsequent pregnancy outcomes were contrasted. To characterize the subsequent pregnancy risk of congenital syphilis, those women with recurrent congenital syphilis were contrasted to women who delivered infants without congenital syphilis. Rapid plasma reagin (RPR) titers in the initial and subsequent pregnancy were analyzed by neonatal outcome. Forty percent of the women who delivered an infant with congenital syphilis in their first pregnancy delivered yet another infant with congenital syphilis in the subsequent pregnancy. Continued cocaine use was the single most important risk factor for delivering another infant with congenital syphilis (p < 0.0001). Forty-two percent of the women who delivered an infant without congenital syphilis in the initial pregnancy delivered an infant with congenital syphilis in the subsequent pregnancy. Birthweight, the number of neonatal hospital days, and the incidence of respiratory distress syndrome (RDS), neonatal pneumonia, abruption, and positive meconium drug screens were not significantly different between the initial and subsequent pregnancies. As with the initial pregnancy, women continued to experience poor pregnancy outcomes in the subsequent pregnancy.