Acute aortic dissection and acute pulmonary embolism are two life-threatening emergencies. The presented case is of an 81-year-old man who has been diagnosed with an acute Stanford type A aortic dissection and referred to a tertiary hospital for surgical treatment. After a successful aortic repair and an overall favourable postoperative recovery, he was diagnosed with cervical and upper extremity deep vein thrombosis and was anticoagulated accordingly. He later presented with massive bilateral pulmonary embolism.