Tracheal perforation is a rare postoperative complication of total thyroidectomy. While previously documented cases have been reported in the anterior aspect of the trachea after a total thyroidectomy, we report what we believe is the first documented case of a perforation in the posterior aspect of the trachea. Our patient was a 29-year-old woman who presented with symptoms of tracheal impingement in the context of a right-sided goiter that subsequent investigation found to be three benign colloid nodules. Fourteen days after her total thyroidectomy, she presented with surgical emphysema surrounding the wound. Computed tomography identified a 2.5-mm defect in the right posterior lateral trachea, posterior to the cartilaginous ring. The defect failed to seal spontaneously, and after 48 hours, the patient remained symptomatic. During reexploration, the defect was successfully repaired with a myovascular transposition flap in conjunction with Tisseel tissue-bonding agent. This technique has the potential to be applied in future intraoperative and postoperative cases of tracheal perforation.