A 57-year-old woman with a history of diabetes mellitus, hypertension, and coronary artery disease presented with recurrent multi-territorial ischemic strokes. Her initial work-up showed unclear etiology. A transesophageal echocardiogram was obtained and demonstrated a 0.5x1 cm mobile echodensity on the mitral valve, concerning for either thrombus or vegetation. Thrombophilic laboratory results displayed an indeterminate lupus anticoagulant cascade. As the patient lacked infectious symptoms with an extensive negative infectious workup, she was started on anticoagulation due to possible thrombotic source in the setting of thrombophilia. However, the patient suffered another ischemic stroke while fully anticoagulated. With this being her third stroke in a seven-month period, the patient underwent surgical resection of the lesion. At the time of surgery, the mass was noted to appear as an infectious vegetation, and she was treated with broad-spectrum antibiotics for presumed culture-negative endocarditis. The valve culture later grew Staphylococcus epidermidis. Daptomycin was continued and she has had no additional strokes to date.