Diffuse idiopathic skeletal hyperostosis (DISH) is characterized by calcification and ossification of ligaments, predominantly affecting the spine. Although often asymptomatic, it can cause dysphagia, dyspnea, and airway obstruction when anterior cervical osteophytes are involved. A 70-year-old male presented with severe dysphagia, respiratory distress, and weight loss. Magnetic resonance imaging (MRI) revealed prominent anterior cervical osteophytes (C2-C7), causing airway narrowing and esophageal compression, consistent with DISH. Acute respiratory failure with stridor required urgent intubation and mechanical ventilation. Due to surgical limitations at the initial hospital, the patient was transferred to a tertiary central facility for specialized care. This case highlights the diagnostic and therapeutic complexities of DISH-related airway obstruction. Multidisciplinary care proved critical, including corticosteroids, mechanical ventilation, and nutritional support. Acute respiratory decompensation may have been triggered by epiglottitis secondary to microaspiration. Early recognition and coordinated multidisciplinary management are essential for achieving optimal outcomes in severe DISH cases involving airway obstruction.