Purpose of Review <p>Rigid support, stable epithelial lining, and vascularization are prerequisites for successful and durable long-segment tracheal reconstruction. This review critically evaluates each of the five main approaches to long-segment tracheal reconstruction using this three-prerequisite framework and highlights recent scientific and clinical advances.</p> Recent Findings <p>Aortic allografts have emerged as one of the most systematically studied techniques, with fifty patients enrolling in the prospective TRITON-01 registry between 2009 and 2025. The first and only case of single-stage long-segment tracheal transplantation was successfully completed in 2021. Autologous tissue flaps are the most widely used and reported approach, with 87 cases published between 2000 and 2025. Despite recent major advances in decellularization protocols, scaffold synthesis, and cellular seeding and conditioning, widespread clinical application of tissue-engineered tracheal grafts will require rigorous preclinical validation in large-animal models and regulatory approval.</p> Summary <p>There is no clearly superior approach to long-segment tracheal reconstruction. Preclinical validation, standardized and prospective outcomes reporting, and large-sample, controlled trials are required to address this challenging clinical question.</p>