A subtle aortic dissection can be challenging to detect despite the availability of multiple diagnostic modalities. Whilst rare, the inability to detect this variant of aortic dissection can lead to a dismal prognosis. We present an extremely rare case of a subtle aortic dissection with supraannular aortic root intimal tear and acute severe aortic regurgitation in a patient with a bicuspid aortic valve. Initial concerns were either aortic dissection or infective endocarditis. Despite advanced multimodality preoperative imaging, diagnosis was made intraoperatively and a Bentall procedure with a mechanical aortic valve was performed. As current data is limited, a literature review concerning subtle aortic dissection is provided.