A 36-year-old male with recent fracture repair and treatment for two superficial deep venous thrombosis (DVT) in the left upper extremity (LUE) presented with LUE allodynia, weakness, and a facial droop after excessive alcohol intake and sun exposure. Exam was remarkable for LUE tenderness and limited mobility. Given his history of DVTs, hypercoagulable state, and new neurologic symptoms, a stroke code was initiated. Stroke work-up was unremarkable, with negative brain and brachial plexus MRI. Patient symptoms persisted even after initiation of gabapentin and heparin, for neuropathic pain and potential CVT, respectively. Cerebral angiography confirmed a VoT thrombosis with no need for mechanical thrombectomy. He was safely discharged with improvement of symptoms on anticoagulation. Patient returned with diagnosis of acute parietal lobe ischemic infarct. Brain MRI completed within 14 days of outside diagnosis did not appreciate an area of restricted diffusion with corresponding apparent diffusion coefficient. Patient was safely discharged with anticoagulants again after ruling out other acute pathology. Neurology and hematology-oncology referrals to rule out other pro-thrombotic conditions were advised on discharge.