Tracheal stenosis represents a significant challenge. Surgeons continue to search for appropriate reconstructive techniques and grafting materials for long tracheal segment reconstruction. Grafts can be classified as synthetic, allogenic, autogenic, transplant, and engineered. Although none of these grafts have provided overwhelming success, acellular composite engineered grafts have shown early promise and can be applied in benign and malignant tracheal diseases. Intraluminal granulation tissue causing re-stenosis is the biggest challenge in tracheal reconstruction. Tracheal wound healing and tissue regeneration pathways must be deeply explored and better characterized to advance the field of tracheal reconstruction.