The rise in stroke cases in young people should be of major health concern, given the extensive compilation of underlying causes not traditionally seen in older people, and the impact and longevity of complications. Cerebral venous sinus thrombosis (CVST) is a rare form of stroke with female predominance. The clinical manifestations of CVST can vary vastly, thus delaying diagnosis and leading to significant morbidity and mortality. Thrombosis induced by inflammatory bowel disease is well appreciated in the literature but not in acute clinical practice. We discuss the case of a young female whose acute presentation of headache and diagnosis of CVST led to the discovery of underlying Crohn's disease. It highlights the importance of recognising unusual presentations of systemic conditions and the role of multidisciplinary teams for accurate diagnosis and effective management.