A 31-year-old immunocompetent, heterosexual man with no relevant medical history presented with 1 week of jaundice, abdominal pain, cough and headache. Examination revealed scleral icterus, right upper quadrant tenderness and hepatomegaly. Initial investigations revealed hyperbilirubinaemia and elevated transaminases. Serum studies were positive for antinuclear antibodies, antimitochondrial antibodies, and herpes simplex virus IgM. Despite being started on intravenous acyclovir, his bilirubin and transaminase levels continued to rise. He was subsequently tested for syphilis given his maculopapular rash on the soles of his feet and it returned positive. He improved clinically with the initiation of penicillin. In this case, we will discuss the presentation, diagnosis and treatment of syphilitic hepatitis.