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Over the past five decades, the incidence of intravenous drug use- (IVDU-) associated infective endocarditis (IE) has been on the rise in North America. Classically, IVDU has been thought to affect right-sided valves. However, in recent times a more variable presentation of IVDU-associated IE has been reported. Here, we report a case of a patient with a known history of IVDU who presented with clinical symptoms concerning for right- as well as left-sided endocarditis. In addition, we also discuss what should be considered adequate evaluation for patients with suspected endocarditis, and more specifically, what should be the role of transesophageal echocardiography in patients with IE noted on transthoracic echocardiography.