Adult tracheomalacia can be caused by long standing goitre or malignant infiltration and has a high morbidity. We anticipated possibility of postoperative tracheomalacia (based on preoperative dynamic cervical sonography and radiographic evidence), in both the cases presented here. A high index of suspicion helped in timely detection of this complication. An algorithm to decode tracheomalacia is constructed here. Elective endotracheal tube (ETT) retention postoperatively, followed by a planned, trial tracheal extubation with gradual ETT withdrawal under bronchoscopic guidance in the OT, several days post-surgery was employed. ETT re-insertion followed by an elective tracheostomy was performed on bronchoscopic confirmation of tracheomalacia.