Type A aortic dissection (TAAD) is a potentially life-threatening diagnosis that can present with elusive symptomatology. A high degree of clinical suspicion is necessary for prompt diagnosis and management. We describe a case of a transthoracic echo (TTE) in a non-suspicious clinic patient diagnosed with TAAD. A 66-year-old Caucasian male presented for a routine clinic visit with one episode of acute severe chest pain. An echocardiogram was ordered for further workup of hypertension and chest discomfort. The echocardiogram demonstrated an ejection fraction of 60% without significant valvular abnormalities. There was suspicion of aortic pathology, which required multiple attending to review the images. The final interpretation was TAAD with a thrombus present in the false lumen. The patient then presented to the Emergency Department. A computed tomographic angiography was performed, which subsequently confirmed the TAAD. The patient was admitted to the cardiovascular ICU and ultimately underwent a successful repair of the dissection. The patient had an unremarkable post-operative course and was ultimately discharged home. Our case demonstrated a diagnosis of TAAD by office-based TTE as the original imaging modality. While this was unconventional, a TAAD should remain on the differential diagnosis when being ordered for the patient's with uncontrolled hypertension with chest pain as a presenting symptom.