An unusual case of two large pseudoaneurysms of the ascending aorta. A large pleural effusion is highly concerning for rupture of the pseudoaneurysm, likely from the caudal one given the thin rim of higher attenuation fluid surrounding the aneurysm sac and lack of significant fluid/stranding about the upper aneurysm within the superior mediastinum. The presence of pleural effusion is often a reactive finding and does not necessarily indicate blood products within the pleural space, as differing densities of the fluid can be appreciated on the original examination. This patient was successfully managed with urgent graft replacement of the ascending aorta.