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Headaches in pregnancy are a common occurrence, and most differentials are benign but cerebral venous thrombosis (CVT) is a life-threatening secondary headache that is more common in pregnancy and postpartum. CVT is caused by an occlusion of the dural venous sinus and/or cerebral veins and presents with various non-specific presentations and has numerous causes and risk factors which make clinical diagnosis difficult. A woman in her late 30s was diagnosed with extensive CVT at 34 weeks gestation after reporting a persistent headache, visual disturbance and intermittent right-sided paraesthesia. This was her second pregnancy and it had been classed as high risk due to body mass index >40 and history of caesarean section. The woman was being managed in the joint obstetric-endocrinology clinic due to gestational diabetes. Diagnosis of CVT was made on magnetic resonance venogram, which revealed a dural sinus thrombosis involving the left transverse, left sigmoid, left jugular bulb and upper part of left internal jugular vein. She was referred to a tertiary centre for joint care of neurology and obstetrics. Treatment with a two times per day dosing regimen of dalteparin was commenced until elective caesarean section at 37 weeks gestation, after which treatment was changed to warfarin therapy for a further 6 months. Her follow-up recovery was good; she remains asymptomatic. This case highlights difficulties in detecting CVT and treatment of CVT in the third trimester of pregnancy.