Aortic dissection is a life threatening emergency. This case illustrates the unusual way an aortic dissection can present. This patient presented with sharp, left interscapular pain, which subsided after a while and left-sided pleural effusion. Further investigations revealed that this was a case of thoracic aortic dissection with a leak into pleural space. She underwent thoracic endovascular aortic repair with stent graft insertion.