Distal hallux gangrene and neuropathic ulceration associated with digit deformity frequently result in osteomyelitis of the distal phalanx. Ideal treatment would involve limited resection to preserve function. We describe our surgical technique and retrospective results for distal Syme hallux amputation with plantar flap closure. An institutional review board-approved review was conducted on cases performed over 8 years. A total of 15 consecutive patients (16 digits) with hallux soft tissue loss who had undergone distal Syme hallux amputation were included. In each case, initial resection removed the distal hallux wound, nail bed, and distal phalanx. The proximal phalanx tip was remodeled, allowing margin biopsy and reduction of prominence. Of the 16 digits, 5 (31.3%) had hammertoe deformity and 1 (6.3%) was excessively long. Positive probe-to-bone status was identified in 8 of the 16 digits (50.0%). All 8 ulcers (100.0%) that probed to bone had histologic or culture results consistent with distal phalanx osteomyelitis. A proximal margin biopsy was taken in 12 of 16 digits (75.0%), and proximal phalanx osteomyelitis was observed in 4 of 12 proximal margin biopsies (33.3%). Two digits (12.5%) failed to heal. Three digits (18.8%) required a more proximal amputation, and the remaining 13 (81.3%) were found to be well-healed and functional at the final follow-up examination. The mean follow-up period was 27.6 (range 8 to 97) months. We have found distal Syme hallux amputation to be an effective treatment when used judiciously for distal hallux gangrene and osteomyelitis associated with neuropathic ulceration. This procedure permits bone biopsy for early diagnosis, confirmation of clean margins, removal of nonviable tissue and the abnormal toenail, and some deformity correction.