The Montgomery T-tube is a versatile silicone stent used in the management of complex tracheal and laryngotracheal disease, specifically tracheal stenosis, tracheomalacia, or post-surgical airway compromise. It serves to maintain airway patency while preserving phonation and eliminating the need for a traditional tracheostomy. The chapter reviews the indications, contraindications, technique of insertion and removal, common complications, and troubleshooting of the Montgomery T-tube. Special consideration for a multidisciplinary management approach in collaboration with interventional pulmonology and otolaryngology for patient selection, device sizing, placement, and long-term care optimize patient outcomes.