A 68-year-old man with a history of medullary thyroid cancer status after resection and radiation was found to have recurrence at routine follow-up. He underwent cervical tracheal resection and reconstruction with left sternocleidomastoid muscle flap buttress. On postoperative day 10, he developed worsening shortness of breath, hypoxemia, and halitosis. Bronchoscopy revealed anastomotic dehiscence at the proximal trachea with areas of necrosis (Fig 1). Biopsy and culture showed polymicrobial flora (Streptococcus viridans, Corynebacterium, and Candida) with possible aspergillosis on the tissue pathology. The patient was treated with broad-spectrum antibiotics (vancomycin, ceftriaxone, and metronidazole) and antifungal (voriconazole) therapy. He underwent neck reexploration, debridement, tracheal resection and reconstruction with AlloDerm (LifeCell Corporation), and tracheostomy tube placement. Subsequently, the patient developed multiple vascular complications, including right carotid artery rupture. After multiple vascular interventions, he ultimately stabilized on postoperative day 35. At this point, he had a tubular-shaped AlloDerm connecting his upper and lower trachea and received aspirin, clopidogrel, and heparin for prevention of vascular stent thrombosis. Given the complex clinical picture and the patient’s desire to be able to phonate, we designed a customized T-tube 8 weeks after his initial surgery.