Diabetic neuroarthropathy is a frequent complication of diabetes mellitus that results in instability of the foot, structural deformity, and soft-tissue breakdown secondary to increased plantar pressure. The midfoot is commonly involved in diabetic neuroarthropathy. Collapse of the medial, lateral, or both longitudinal arches may result in increased plantar pressures and subsequent midfoot ulceration. The majority of these wounds can be managed with local wound care, off-loading, and other forms of nonoperative care. Surgical intervention becomes necessary when the wound fails to heal with conservative measures. The authors performed a retrospective review of patients who underwent ostectomy for chronic or recurrent ulceration in the midfoot secondary to diabetic neuroarthropathy. The authors reviewed 27 procedures in 20 patients. There were 18 medial ulcers and 9 lateral ulcers. Wounds had resolved in 20 of 27 cases for 74% healing rate. The majority of failed procedures involved lateral column wounds (six of seven). Revisional surgery was required in five of the nine lateral column wounds for limb salvage. There was a statistically significant difference between the rate of complications by ulcer location (p = .00174). The rate of complications was significantly higher for lateral column ulcers. These results indicate that ostectomy is a reasonable option for medial column ulcers that fail nonoperative care. However, ostectomy for ulcers involving the lateral column is less predictable and failure often requires complex reconstructive soft tissue and osseous procedures for limb salvage.