The combined pathology of intra-mural haematoma (IMH) and penetrating aortic ulcer (PAU) represents disease progression of the PAU with high risk for further progression to either rupture or pseudo-aneurysm formation, and hence surgical intervention should be offered once diagnosis is made regardless of the presentation. We present a 70-year-old fit lady with chronic type A IMH associated with multiple PAUs, diagnosed incidentally, the patient underwent urgent surgical repair with good outcome.