Aortic dissection is a life-threatening emergency associated with significant mortality rate. Early diagnosis is essential to improve the survival. Although the most common presentation is severe chest pain, it can be variable leading to delay in the diagnosis especially if it is painless. Painless aortic dissection is a rare entity with sparse data available based on case reports. We present a case of a young male with an atypical presentation where the presumptive diagnosis of infective endocarditis was made based on initial presentation but was eventually diagnosed as painless aortic dissection.