We report the case of recurrent occlusion in the middle cerebral artery (MCA) with carotid web of the internal carotid artery (ICA). There is a paucity of data on strategy of secondary prevention for carotid web. A 65-year-old women presented with the sudden onset of global aphasia and right-sided weakness. She had no history of hypertension, diabetes, and hyperlipidemia, and cardiac disease. Her NIHSS score was 25. Computed tomography angiography (CTA) demonstrated occlusion in the left middle cerebral artery (MCA) and a shelf-like filling deficit emanating from the posterior wall of the right ICA. Complete recanalization with full representation was rapidly achieve with mechanical thrombectomy (MT) using a retrieval stent. Transthoracic echocardiography and inpatient cardiac telemetry did not show any abnormalities. At 7 days after admission, the patient had fully recovered. Since then, she has been taking clopidogrel. After 30 months, she presented with the sudden onset of language disturbance. CTA showed occlusion in the left MCA. Complete recanalization was rapidly achieving with MT. Diffusion weighted MR imaging showed high signal intensity in several areas within left MCA territory. At discharge, she had 2 score of NIHSS at discharge and was taking warfarin. The high rate of recurrent stroke while on antiplatelet therapy suggests a need for aggressive treatment when a carotid web is detected ipsilateral to an acute stroke. Given the nature of blood stagnation distal to the lesion, anticoagulation is one attractive possibility for treatment given that the clot likely yields fibrin-rich emboli as opposed to aggregated platelets.