Collapsing trachea is a common obstructive airway disease predominantly affecting small breed dogs. While most patients can be managed medically, minimally-invasive intraluminal tracheal stenting is used in refractory cases. This case report describes a 9-year-old Yorkshire Terrier with a tracheal stent that fractured after 3 years, requiring the placement of a new stent. Stent failure was attributed to atypical morphology of the focal tracheal collapse. Discussed are the risk factors and pathogenesis of collapsing trachea, medical and surgical management, and the anesthetic considerations taken in patients with obstructive airway disease.