Introduction: Aortic Dissection (AD) results from a tear between the layers of the aorta. This is often seen among older males or those with heritable connective tissue disorders, and it mostly presents as chest pain. Management involves surgical repair wherein post procedure complications are to be expected. Mediastinitis, or deep sternal wound infection, however, is likewise unusual. Case Presentation: We present a case of a 29-year-old Filipino male presenting with sudden diffuse abdominal pain; he had no comorbidities and had no significant history suggestive of connective tissue disorders. Physical examination was mostly unremarkable. CT Aortogram revealed presence of dissection from the proximal ascending aorta up to the common iliac arteries, with the entry tear measuring 8.5mm at the level of T5, with extension to the proximal branches of the aortic arch, both common carotid arteries, right renal, right internal and external iliac arteries. Echocardiogram also showed a normal aortic valve but with dilated sinus of Valsalva(4.5cm, z-score 5.13). The patient underwent a Modified Bentall Procedure with Cabrol Shunt, with delayed closure of operative site due to extensive bleeding. Cystic medial necrosis was not seen on biopsy. After developing persistent post-operative fever, repeat chest CT showed a fluid collection in the mediastinum encasing the ascending aorta and main pulmonary trunk; culture of abscess fluid was positive for Candida tropicalis . He was then given prolonged parenteral followed by oral antifungal therapy and subsequently discharged improved. Discussion: Vascular causes of abdominal pain should be considered in patients with scant history and physical findings. Major vascular surgery has expected complications such as bleeding and infection; the management of such complications should incorporate a multidisciplinary approach as in such cases, a trial of medical management may be safer than repeat surgery.