Background: Hemiplegic migraine is a rare phenomenon of migraines characterized by transient motor weakness. It may closely mimic acute ischemic cerebrovascular events, particularly in patients with vascular risk factors. This can be a diagnostic challenge especially in patients with previous hypercoagulable history. Case Presentation: A 31 year old female with a past medical history of right upper extremity DVT, first trimester miscarriage at 8 weeks gestation, migraines, and antiphospholipid antibody syndrome presented with sudden onset right arm and right leg weakness accompanied by a throbbing right sided headache. Her headache was her typical migraine-like headache, including nausea, vomiting, photophobia, and phonophobia, but her right sided weakness was new. She denied any family history of migraines. On arrival to the emergency department, her vitals were stable. On physical examination, she was found to have 3/5 weakness in the right upper and lower extremity. No facial droop or other neurological manifestations were noted on physical exam. Given her hypercoagulable history, an acute cerebrovascular accident was suspected. A CT of the head was negative for any bleed. A CTA of the head and neck was positive for moderate occlusion of her right vertebral artery at the distal V2, V3, and V4 segments. An MRI of the brain was negative. The patient was started on Aspirin 81 mg and Plavix 75 mg after consulting neurosurgery for the occlusion. Stroke was ruled out and after treating the patient’s headache and nausea with antiemetics and the migraine cocktail of IV Ketorolac, IV Diphenhydramine, and IV fluids, the weakness slowly improved and almost went away completely. Given the patient’s resolution of symptoms following migraine treatment, neurology was concerned for hemiplegic migraine and the patient was discharged with referral to a tertiary care center for genetic testing. The patient was tested for genetic mutations in CACNA1A, ATP1A2, and SCN1A. She tested positive for CACNA1A and was diagnosed with hemiplegic migraine and started on appropriate management. Discussion: This case illustrates the diagnostic complexity of acute unilateral weakness in a young female patient with hypercoagulable risk factors. The patient’s symptoms, along with negative MRI and rapid resolution of symptoms with migraine directed therapy, favored a diagnosis of hemiplegic migraine rather than an acute ischemic stroke. Conclusion: Hemiplegic migraine should remain in the differential in patients with unilateral weakness accompanied by headache and negative imaging. Prompt imaging and detailed evaluation are essential to prevent unnecessary thrombolysis in patients with hypercoagulable disorders.