Introduction Spinal stenosis has a wide range of causes including disc herniation, facet hypertrophy, degenerative spondylosis, facet cyst, ossification of the ligamentum flavum (OLF) and ossification of the posterior longitudinal ligament (OPLL). We present three cases of diffuse spinal hyperostosis causing severe spinal stenosis and myelopathy, which demonstrate a unique association between obesity and a novel syndrome of hyperostosis. Case Presentation This report describes 3 morbidly obese patients with diffuse spinal hyperostosis causing critical thoracic stenosis. Their presenting complaints focus on lower extremity weakness and the CT/MRI imaging is striking for diffuse hyper-ossification at thoracic levels. Two patients were subsequently managed with spinal decompression, and one patient was managed non-operatively. Discussion Metabolic changes associated with obesity may result in diffuse hyperostosis with ligament ossification and spinal stenosis. Pre-operative imaging is essential to identify the degree of ossification and potential dural involvement as this may complicate management.