Aortic dissection (AD) is a life-threatening emergency involving a tear in the aortic intima, leading to a false lumen. Atrial fibrillation (AF) can complicate AD, increasing management challenges and mortality risks. We report a 67-year-old male with no known past medical history who presented with a 1-day history of abdominal pain. Initial examination showed mild hypertension, elevated bilirubin level, and leukocytosis. Imaging studies indicated gallbladder distension with cholelithiasis. Discharged with outpatient follow-up for elective cholecystectomy, the patient returned 2 days later for preoperative clearance, was hypertensive and tachycardic, presented with atrial flutter, and was referred to the emergency department. A 2D echo showed left ventricular ejection fraction (LVEF) 35% to 40% and pericardial effusion. Transesophageal echocardiography (TEE) revealed LVEF 50% to 55% and no thrombus, converting to sinus rhythm postcardioversion. The TEE also suggested type A AD, confirmed by computed tomography (CT) angiography, showing dissection from the aortic valve to the left external iliac artery with pericardial effusion. Emergent surgical repair was performed, and the patient was stabilized and discharged with follow-up. This case illustrates the complexity of diagnosing and managing AD, especially with concurrent AF. Recognizing the association between AD and AF is essential as AF increases in-hospital mortality in AD patients.