A 68-year-old man with recurrent medullary thyroid cancer underwent cervical tracheal resection and reconstruction. His course was complicated by tracheal anastomotic dehiscence, right carotid blowout, and ultimately cervical tracheoplasty with AlloDerm. Given the complex vascular interventions and upper-airway anatomy, a custom-designed Montgomery T-tube was designed for him. Three-dimensional digital reconstruction of his upper airways was obtained from a CT scan. The T-tube was designed and fabricated based on the digital trachea model and was subsequently placed successfully. Follow-up CT scan and bronchoscopy confirmed placement and revealed no granulation tissue at 4 weeks. The patient was discharged to home with the ability to phonate. To our knowledge, this is the first demonstration of three-dimensional modeling of an upper-airway defect with subsequent T-tube design using engineering software. The success of this case demonstrates a possible avenue for personalized airway prosthesis design and manufacturing in the future.