Radiologic evidence of aortic disease is not always consistent with the diagnosis. With lack of accompanying symptoms or with an atypical presentation, diagnosis of aortic pathology relies greatly on imaging techniques. We report the case of a 58 year-old female who presented with incidental radiographic findings consistent with a type A aortic intramural hematoma and a vague left-sided chest discomfort. After follow-up imaging was consistent with disease progression and hematoma expansion, the affected segment was resected and pathology reported lymphoplasmacytic aortitis as the underlying etiology of the imaging findings rather than an intramural hematoma. The patient lacked symptoms or serology consistent with rheumatologic disease and the postoperative course was uneventful. The management of a suspected ascending intramural hematoma is controversial, especially when the patient presents with atypical signs and symptoms. Features of disease progression may warrant urgent surgical intervention.