Aortic dissection is a rare life-threatening condition that typically presents with acute onset of severe chest, abdominal, or back pain. Some patients might present with atypical symptoms and findings, such as neurological syndromes, making it difficult to make the diagnosis. Here, we report a case of a painless acute aortic rupture over an already existing Stanford type A chronic aortic dissection in a 59-year-old patient, with prevalence of neurological symptoms. The aortic dissection presented as recurrent episodes of dizziness/syncope and transient amnesia. We believe it is important to report this case because of the rare clinical presentation of aortic dissection, raising the awareness and diagnosing level of atypical aortic dissections.