In this case report, we discuss the diagnostic dilemma presented by a patient admitted for elevated liver enzymes and rash, who had a history of recent amoxicillin use. This presentation initially appeared to fit the criteria for Drug Reaction with Eosinophilia and Systemic Symptoms (DRESS) syndrome. However, histologic evaluation determined the rash was consistent with Miliaria rubra rather than the lymphocytic infiltrate of DRESS. This necessitated broad diagnostic testing to determine the underlying etiology of the patient's syndrome. Serology subsequently demonstrated primary Epstein-Barr Virus (EBV) infection, which explained her acute liver injury. Her eosinophilia was potentially related to an allergic reaction to surgical tape but was never definitely diagnosed. This case demonstrates the importance of maintaining a wide differential even when clinical diagnostic criteria are apparently met.