We present a case of a 78 years old man who was suffering from worsening shortness of breath and cramping lower abdominal pain for last 4 days. The computed tomography (CT) scan of chest showed some pulmonary nodules of 5mm in size and a pancreatic neck mass 3.7 x 3.5 cm with hepatic metastases, ascites, 3.4 cm abdominal aortic aneurysm. Ultrasound Doppler of lower extremities showed echogenic thrombus within the right lower extremity from the common femoral vein through the popliteal vein. The patient was already on warfarin for atrial fibrillation on admission and presented with supra-therapeutic international normalized ratio (INR) but without any bleeding event. Later,  he developed right upper extremity weakness and left sided hemianopsia that led to computed tomography (CT) angiography of head which showed right occipital acute infarction. Despite transitioning to LMWH from the VKA, the patient suffered from ischemic stroke. The VKA treatment can lead to recurrent thrombosis despite the supra-therapeutic INR with malignancy highlighting an anti-coagulation failure.