Mediastinal pseudocysts can pose a diagnostic and therapeutic challenge to the clinician and surgeon. Recognizing their presence and instituting appropriate therapy can reduce morbidity and mortality. This report describes unusual clinical features in a patient presenting with multiple mediastinal pseudocysts due to pancreatic duct leak secondary to pancreatic duct stenosis and an entrapment of a pancreatic duct stone. Successful endoscopic therapy averted the need for surgery.