Spontaneous oesophageal rupture has been a known ailment with a high morbidity and mortality. Various factors contribute to its predisposition such as preexisting oesophageal diseases, increased intraluminal pressure, neurogenic causes, and iatrogenic-commonest being instrumentation. We present the case of a 26-year-old male with features of right hydropneumothorax for which an intercostal chest drain (ICD) was inserted that yielded turbid fluid with suspicion of it being gastric contents. With a diagnosis of diaphragmatic hernia and gut/bowel injury caused due to intercostal drain, the patient underwent emergency exploratory laparotomy. No abnormality was detected and possibility of oesophageal injury/rupture was contemplated though ruled out on investigations. The patient improved with medical treatment of empyema and discharged. The patient was lost to follow-up until after a year the patient reported to surgery OPD with complaints of dysphagia. A barium swallow revealed thoracic oesophageal benign stricture thus confirming our suspicion of spontaneous oesophageal rupture that had occurred a year ago. Knowledge about atypical presentations of oesophageal rupture is important so as to be more aware of this possibility.