The authors present a technical note for a prone positioning system developed to facilitate cervical extension osteotomy for ankylosing spondylitis in the presence of severe deformity and frailty. Chin-on-chest deformity represents one of the most debilitating changes of ankylosing spondylitis. Where the chin-brow angle approaches or exceeds 90°, prone positioning becomes problematic due to the fixed position of the head. Furthermore, the challenge is compounded where physiological deconditioning leads to frailty, and the side effects of medical therapies decrease muscle mass and skin quality. Conventional prone positioning equipment is not able to cater to all patients. A versatile system was developed using a 3D reconstruction to enable a positioning simulation and verification tool. The tool was used to comprehensively plan the perioperative episode, including spatial orientation and associated equipment. Three-dimensional printing was used to manufacture a bespoke positioning device that precisely matched the contours of the patient, reducing contact pressure and risk of skin injury. The authors were able to safely facilitate surgery for a patient whose deformity and frailty may otherwise have precluded this possibility. The system has potential safety and economic implications that may be of significant utility to other institutions engaging in complex spinal surgery.