A 25-year-old pregnant woman (first trimester) with bilateral middle cerebral artery (MCA) territory infarcts sustained during childhood due to MMD underwent indirect synangiosis 15 years ago. During her first pregnancy (2018), she developed pre-eclampsia, but no complications related to MMD. Over the past year, prior to current conception, she experienced episodes of right sided numbness concerning for transient ischemic attack (TIA), lasting a few minutes, typically preceded by hyperventilation during anxiety attacks. She underwent CT perfusion (CTP) with acetazolamide challenge showing a relative reduction in perfusion in the left MCA/PCA (posterior cerebral artery) borderzone territory. She presents now with similar TIA symptoms that lasted longer than usual. On evaluation, she was anxious, mildly hypertensive with a normal neurological exam with complete resolution of symptoms. She is compliant with aspirin. Referrals to high-risk obstetrician and behavioral health providers were placed. She was discharged with instructions to continue aspirin, monitor blood pressure (BP) at home and mindfulness techniques to help manage anxiety.