Acute aortic syndromes (AAS) include life-threatening conditions like penetrating atheromatous ulcer (PAU), which occurs when an atherosclerotic plaque erodes through the aortic wall. This can lead to complications such as intramural hematoma, pseudoaneurysm, or aortic rupture, especially in the ascending aorta. PAUs typically affect older males with atherosclerosis and are most commonly found in the lower descending thoracic aorta, with multiple PAUs being rare. This report highlights a case involving the incidental discovery of multiple PAUs and an associated ductus diverticulum, and it discusses their presentation and management. An 88-year-old male with a history of hypertension, diabetes, and pulmonary fibrosis presented with right-sided upper quadrant and chest pain radiating to the back. Initial imaging suggested progression of pulmonary fibrosis or an infection, but a subsequent CT angiogram revealed at least 12 focal outpouchings in the distal aortic arch and proximal descending thoracic aorta, compatible with PAUs. Additionally, a ductus diverticulum was identified. The patient was managed with high-dose statin therapy and scheduled for follow-up CTA in three months. This case highlights the incidental discovery of multiple PAUs and a ductus diverticulum, underscoring the rarity and complexity of PAU presentations. It emphasizes the importance of including PAU in the differential diagnosis for patients presenting with chest pain, especially when symptoms are atypical or overlap with other conditions. Early identification and management are crucial to prevent severe complications such as aortic dissection or rupture.