Abstract: Boerhaave's syndrome is a rare but lethal disease involving the gastrointestinal tract. It is a spontaneous esophageal perforation with complete transmural tear caused by a sudden increase of intraluminal pressure in the esophagus. The disease is associated with high mortality of more than 40% with early surgical intervention. Delayed surgical intervention more than 7 days after the initial presentation is associated with nearly 100% mortality. The classical Mackler's triad of symptoms is rare. The reported rate of misdiagnosis is high. Delayed presentation, misdiagnosis, and intervention is associated with poor healing, increased complications, prolonged hospital stay, and increased mortality. We report two cases of Boerhaave's syndrome. One case presented early within 24hours with classical symptoms, while another presented late after 7 days with atypical symptoms and a delayed diagnosis elsewhere. Both the cases where managed by recommended standard practices. Despite minimal complications, the patient with early presentation had a comparatively good healing, early recovery, and short hospital stay. The patient with delayed presentation had already developed multiple complications at presentation to our setup. Though this patient required a prolonged hospital stay, an intensive, imaginative, and aggressive multidisciplinary care resulted in a good recovery. A high index of suspicion and early intervention helped in the recovery and prevention of complications in patients presenting early. Good multidisciplinary care resulted in a good recovery in the patient with delayed presentation. With a good and imaginative multidisciplinary care, even a condition with a mortality rate as high as 100% can be managed successfully. Keywords Boerhaave Syndrome, Mediastinitis, Esophageal Perforation.