Secondary syphilis has variable systemic manifestations, impersonating the presentation of more common pathologies, deceiving clinicians, and creating a difficult-to-diagnose patient. The case discussed combines hepatic syphilis with an uncommon syphilitic dermatologic presentation in a patient with HIV and a history of hepatitis A and B. Due to the challenge of diagnosis, the relative ease of confirming the diagnosis with serological assays, and reversibility of hepatic injury, the inclusion of syphilitic hepatitis on a differential diagnosis of hepatitis is warranted.