A 68-year-old man with a background of severe active rheumatoid arthritis (RA) was admitted to Intensive Care Unit (ICU) for respiratory support due to COVID-19 infection. Two days after an elective and uneventful intubation he developed severe and worsening surgical emphysema affecting his face, neck and both upper limbs. Ventilation was difficult to be achieved. Based on a negative chest X-ray, a CT scan of the chest was organized which showed extensive pneumomediastinum with no obvious cause. Therefore, urgent bronchoscopy was performed which showed a glassy lesion/laceration measuring 2 cm × 2 cm at the level of mid-trachea but no other signs of penetration through the airways were noted. Since events appeared 2 days after intubation, this was perceived as secondary to trauma during intubation on an inflammatory process background from RA and COVID-19 in the airways. The endotracheal tube was progressed beyond the site of laceration and bilateral pectoral fasciotomies were performed with negative suction vacuum dressings, which was successful in decreasing the surgical emphysema and achieving decreased ventilation requirements. Despite multi-organ support the patient continued to deteriorate and unfortunately passed away a week following admission. This scenario hightlighted that endotracheal sequalae should be suspected in patients with similar background and presentation.