Aortic dissection is a relatively uncommon, although catastrophic, disease which requires early and accurate diagnosis and treatment for patient survival. Aortic dissection can be difficult to diagnose due to the diverse symptom presentation, which can lead to later diagnosis, resulting in a higher mortality rate. Here we present a case of type A aortic dissection with a varied symptom presentation, highlighting the importance of early detection and the Bentall procedure for management of such cases. A 50-year-old man with no known medical history presented with bilateral lower extremity swelling and fatigue for 2 weeks. The patient denied any chest pain or dyspnoea. Vital signs showed blood pressure of 160/76 mmHg, pulse of 103 bpm, respiratory rate of 18, and temperature of 36.7°C. Laboratory findings indicated a BNP of 1901 pg/ml and troponin of 0.5 ng/ml. An initial diagnosis of decompensated heart failure was made, and IV Lasix was started. Subsequently, an echocardiogram indicated an EF of 50–55% and ascending dissection of the aorta. A CT angiogram of the chest and abdomen confirmed this diagnosis. This patient presented with unusual symptoms of aortic dissection without the typical presentation of chest pain. It is important to consider aortic dissection in a cardiac-related case as prompt imaging can help confirm the diagnosis. We explore the risks and benefits of the Bentall procedure for the management and early detection of aortic dissection.