Boerhaave syndrome, a rare yet frequently fatal diagnosis, is characterized by the spontaneous transmural rupture of the esophagus. The classic presentation of Boerhaave syndrome is characterized by Mackler's triad, consisting of chest pain, vomiting, and subcutaneous emphysema. However, Boerhaave syndrome rarely presents with all the features of Mackler's triad; instead, the common presentation of Boerhaave syndrome includes chest or epigastric pain, severe retching and vomiting, dyspnea, and shock. These symptoms are typically misdiagnosed as cardiogenic in origin. Due to its atypical presentation, rarity, and mimicry of emergent conditions, diagnosis of Boerhaave syndrome is often delayed, resulting in a high mortality rate at the time of diagnosis and with a subsequent exponential increase in mortality if treatment is delayed by greater than 48 hours. Here, we report two atypical presentations of Boerhaave syndrome presenting as tension hydropneumothorax and review ten previously reported cases of Boerhaave syndrome presenting as tension hydropneumothorax. This review serves to raise clinician awareness about the expansive and elusive ways by which esophageal perforation may present, and thereby facilitate timely and potentially life-saving diagnosis.