Laryngectomy and pharyngectomy are surgical options for advanced laryngeal or pharyngeal squamous cell carcinoma. Cervical osteomyelitis-diskitis, occurring when there is dehiscence of the posterior neopharyngeal wall, is an uncommon complication of laryngopharyngectomy. This case series describes imaging findings of pharyngoesophageal wall breakdown with subsequent cervical spine infection and demonstrates that most of these patients had undergone prior esophageal or neopharyngeal dilations for benign posttreatment stricture. Neck pain, fever, or serologic evidence of infection should prompt careful evaluation for osteomyelitis-diskitis and assessment for neopharyngeal breakdown and sinus tract formation, especially in the postdilation setting.