Acute aortic dissection (AAD) is a serious medical problem that requires prompt recognition in order to prevent deadly complications. Nevertheless, making the diagnosis can often be challenging. The clinical signs and symptoms of AAD may vary depending on the location of the dissection, leading to subtle differences in the initial patient presentation. Moreover, the classically described signs of blood pressure disparity, pulse deficit, or the presence of a diastolic murmur are often absent. Here, we report a challenging case of AAD in which the patient presented with acute substernal chest pain that resolved after a short period and was associated with hypotension. His bilateral upper and lower extremities were well perfused with symmetrical, palpable pulses. The initial point-of-care ultrasound (POCUS) showed a small pericardial effusion, and a follow-up echocardiogram revealed an ascending aortic flap with aortic root dilation diagnostic of AAD. Our aim is to shed light on the challenge of diagnosing AAD.