This case of infective endocarditis masquerading as mixed cryoglobulinemia in a man with a history of intravenous drug use (IVDU) and hepatitis C virus (HCV) highlights the importance of maintaining a broad differential and continually re-evaluating the working diagnosis as new information presents itself. The patient presented to an outside hospital and was treated for presumptive mixed cryoglobulinemia with corticosteroid therapy. When the patient did not improve, he was transferred to a tertiary care center for possible Rituximab and/or plasmapheresis. Further investigation revealed Enterococcus bacteremia with subsequent workup consistent with infective endocarditis (IE). This case highlights a diagnostic dilemma and demonstrates the importance of a thorough evaluation as it pertains to overlapping features of IE and mixed cryoglobulinemia.