A 58-year-old female with long-standing history of smoking and hyperlipidemia presented to outside hospital (OSH) with pressure-like headache on top of her head and feeling of facial swelling. CT angiogram of head and neck (CTA) showed right internal carotid artery (ICA) stenosis of 85% and left ICA stenosis of 80%. Three months after the initial presentation she underwent right CEA. Immediately following procedure, she had severe throbbing headache on right side which responded to Toradol. Neurologic examination was otherwise unremarkable, and she was discharged home on dual anti-platelet therapy. After discharge, she continued to have headache. Ten days after the procedure, she developed left sided weakness and presented to an outside hospital where she had a seizure and was started on levetiracetam. MRI of the brain showed edematous changes on the right consistent with CHS without evidence of acute stroke. Right ICA was patent and there was segmental vasoconstriction and dilation of cerebral vasculature consistent with RCVS. Due to increased risk of hemorrhagic strokes with CHS and RCVS, left CEA was not recommended and maximal medical therapy was recommended. There was resolution of edematous changes in right cerebral hemisphere on MRI two months later. CTA at two months follow up showed resolution of segmental vasoconstriction and vasodilation, patent right ICA and unchanged left ICA stenosis.