Introduction: Syphilis, infamously known as the “great imitator,” is an infectious disease caused by the spirochete Treponema pallidum and can affect many organs. Though uncommon, syphilis can also affect the liver, often manifesting as elevated liver enzymes. Herein we describe the case of a 48-year-old immunocompetent male who was found to have a syphilis-induced acute liver injury. Case Description/Methods: A 48-year-old male presented with a two-week history of dry cough, fever, anorexia, and sore throat. He initially presented to an outside hospital where he was diagnosed with community-acquired pneumonia and discharged on amoxicillin-clavulanate. Given poor improvement in symptoms, he presented to our emergency department several days later and noted additional symptoms of headache, blurry vision, and rash. On admission, liver enzymes were elevated (Table 1), and a mild maculopapular rash was noted on his trunk and extremities. Clinical findings and liver injury were attributed to a drug injury in the setting of recent amoxicillin-clavulanate use. However, the liver injury persisted, prompting additional evaluation. Acute and chronic liver serology tests were unrevealing except for a positive anti-mitochondrial antibody, 44 units, and anti-nuclear antibodies, titers of 1:160. Syphilis screen with rapid plasma reagin was reactive with a titer of 1:32. Given neurological symptoms, a lumbar puncture was performed and revealed a reactive fluorescent treponemal antibody test absorption test. The patient was diagnosed with secondary syphilis complicated by neurosyphilis and syphilitic hepatitis. The patient completed a two-week course of intravenous penicillin with complete resolution in symptoms. After initiation of penicillin, the patient's liver chemistries downtrended and normalized after treatment, confirming the diagnosis of syphilitic hepatitis. Discussion: Syphilitic hepatitis is an uncommon manifestation of syphilis. Suspicion should be raised in patients with elevated liver chemistries, in particular cholestatic pattern, who also have manifestations such as maculopapular rash, low grade fever, arthralgias, headache, and changes in vision. This case highlights the importance of maintaining a broad differential and avoiding anchoring bias when approaching elevated liver chemistries. Table 1. - Liver Function Tests Baseline Outside Hospital Presentation Week 1 Week 3 Alkaline phosphatase (IU/L) 78 1126 1118 997 437 ALT (IU/L) 14 225 231 224 53 AST (IU/L) 19 130 154 139 37 Total bilirubin (mg/dL) 0.8 1.9 4.3 2.0 0.9