Ultra-low-dose combination estrogen-progestin contraceptive pills (OCP) have been marketed as being safer to use than previously higher estrogen-containing OCPs. While multiple large studies have shown a dose-dependent association between estrogen and deep vein thrombosis, there remains sparse guidance or data as to whether patients with sickle cell trait should avoid estrogen-containing OCPs regardless of the dosage. We present a case of a 22-year-old female with a history of sickle cell trait who had recently been started on an ultra-low-dose norethindrone-ethinyl estradiol-iron (1-20 mcg) that presented with headache, nausea, vomiting, and obtunded. Initial neuroimaging was significant for an extensive superior sagittal sinus thrombosis with extension into the confluence of dural venous sinuses, right transverse sinus, right sigmoid sinus, and right internal jugular vein which ultimately required systemic anti-coagulation. Her symptoms largely resolved within four days after starting anti-coagulation. She was discharged on day six to complete a six-month course of oral anti-coagulation. At her neurology follow-up three months later, the patient reported resolution of all symptoms. This study evaluates the safety of ultra-low-dose estrogen-containing contraceptive pills in the sickle cell trait population with special focus on cerebral sinus thrombosis.