The majority of esophageal perforations are iatrogenic in nature. Contrast esophagogram is the diagnostic study of choice for diagnosis. It should be conducted first with water-soluble contrast, and repeated with barium if the initial study is equivocal. A detailed history about recent upper endoscopy procedures, bouts of emesis, and blunt thoracic trauma is key to arrive at a prompt diagnosis and treatment. Short interval from recognition to treatment is paramount for patient outcomes.