Forestier’s disease is a systemic, degenerative metabolic condition, which is still insufficiently investigated and understood, characterized by the progressive ossification of the ligaments and entheses. This case describes a 63-year-old man admitted to our department after several years of failed attempts to obtain a definitive diagnosis presenting with a painless mass in the pre-auricular region, gradually worsening dysphonia, severe dysphagia relating to solids, stiffness, and mild pain at the back of the neck. After performing further diagnostic tests, in addition to a pleomorphic adenoma, the simultaneous presence of diffuse spondylarthrosis on the cervical spine was highlighted, with beak-like osteophytes at C2–C5 resulting in esophageal compression. Given the absence of upper digestive endoscopy abnormalities, we initiated an intense logopedic and postural rehabilitative treatment, which led to a significant improvement in the patient’s dysphagia symptoms. In addition, we limited the use of medical therapy to solely indomethacin in order to control the osteophytic process.