Congenital syphilis occurs as a result of maternal transmission of treponema pallidum in utero. This condition is mainly diagnosed by treponemal and non-treponemal serologic tests. However, both maternal nontreponemal and treponemal IgG antibodies can be transferred through the placenta to the fetus, thus complicating its interpretation soon after birth. We report a case of a neonate with congenital syphilis whose mother became infected after the first trimester of pregnancy. We report how skeletal radiographs expedite the clinical decision-making process and direct further management of neonates. This case also highlights the need for repeated syphilis screening in the latter part of pregnancy.