Despite a plan in 1999 by the CDC to eradicate syphilis, the United States has seen a resurgence in syphilis cases; with this resurgence, there has been a concomitant rise in the number of cases of congenital syphilis. Congenital syphilis is both preventable and treatable, yet a combination of factors such as high -risk sexual behavior, ethnic disparities, low socioeconomic status, missed screening and prevention opportunities, and a lack of prenatal care have led to the increased number of neonates who are born with congenital syphilis, whether clinical manifestations are immediately apparent or manifest years later. Inconsistent maternal syphilis screening during pregnancy contributes to missed diagnostic and curative opportunities, fetal infection, and resultant mortality and morbidity risks. We present a neonate born to a 36 y/o G7P5015 African American female EGA who had not received any prenatal care and presented for a fetal echocardiogram due to the presence of congenital heart disease in one of her other children. During the fetal echocardiogram, she developed contractions and was sent to labor and delivery. Due to the unstable condition of the fetus, an urgent Cesarean section was performed. The neonate was found to have poor tone, weak cry, and birth weight. Physical exam revealed peeling of the skin of the palms and soles, and bluish lesions scattered over the chest, abdomen, and shin. Imaging revealed syphilitic osteochondritis in the long bones, and the periosteal reaction was seen in the left humorous and the forearm. Ten days later, the neonate developed further clinical complications including hepatosplenomegaly, syphilitic pneumonia, and a severe rash. This case illustrates a severe presentation of congenital syphilis and emphasizes the crucial need for syphilis screening and treatment throughout pregnancy, as well as testing at delivery if no screening has been done. Clinicians should be especially wary regarding particularly vulnerable patients with one or several critical risk factors.