Three cases of spontaneous rupture of the distal esophagus are presented. All three patients presented in acute distress, exhibiting epigastric pain and signs of cardiovascular collapse. They all underwent surgery for repair of the lesion. One died postoperatively, and the other two patients recovered after a complicated postoperative period. Because Boerhaave syndrome has a high mortality rate and its diagnosis can be elusive, a high index of suspicion should be maintained by the attending physician.