Painless aortic dissection (PAoD) has been previously linked to poor outcomes. We recently encountered a case of a patient with PAoD presenting with dyspnea; the clue to diagnosis was the presence of a loud aortic diastolic murmur. A systematic review of the literature revealed 86 other cases, 62% of which occurred in men with a mean age of 65 years. Left-sided neurologic deficits were the most common presentation, followed by dyspnea and bilateral lower extremity deficits. Pulse asymmetry was found in 53% of patients, as 29% had right-left asymmetry and 24% had upper-lower asymmetry. Cumulatively, 88% of the cases were type A dissection and 51% of the patients died. Erroneous application of fibrinolysis and anticoagulation occurred in multiple instances. PAoD is rare but potentially fatal; a high index of suspicion and a thorough cardiovascular examination are needed to establish the diagnosis before applying possible harmful interventions such as fibrinolysis, vasodilation or anticoagulation.