Acute dissection of the aorta can be one of the most dramatic cardiovascular emergencies. Classically, aortic dissection presents as sudden, severe chest, back, or abdominal pain that is characterised as ripping or tearing in nature. However, a timely diagnosis can be elusive in the event of an atypical presentation. In this report, the authors present two patients with painless aortic dissection who were misdiagnosed during their initial evaluation in the emergency department.