Orogastric tube (OGT) insertion is a routine procedure in medical care. It is often inserted in patients after endotracheal intubation. OGT insertion is often a blind procedure. Misplacement of the tube can cause a variety of complications and can sometimes be life-threatening. We present the case of a 71-year-old male patient who experienced a rare proximal esophageal perforation as a complication of blind insertion of the OGT; he required OGT insertion after receiving endotracheal intubation for hypoxic respiratory failure secondary to COVID-19 infection. The esophageal perforation was revealed on a post-procedural roentgenogram and confirmed by a subsequent computed tomography of the chest. Given the small size of the perforation and the absence of clinical instability, conservative management was pursued leading to improvement of the mediastinitis. Although the complications of OGT insertion are uncommon, their consequences can be potentially serious and require a high degree of suspicion.