Introduction: Diabetes-related tip of lesser toe ulcers are typically associated with underlying hammertoe contracture and peripheral neuropathy. The combination of digital deformity and neuropathy commonly results in non-healing, deep sores that frequently become complicated by osteomyelitis. This condition can rapidly progress to limb threatening infection requiring costly treatment and potential limb loss. We report on a well-known, but poorly reported, technique for surgical management of non-healing tip of lesser toe ulcers. Methods: After approval by the IRB, a retrospective review was performed on patients that underwent officebased distal Symes toe amputation for a non-healing tip of lesser toe ulcer over the past 6 years (2007-2012). A variety of clinical, laboratory, and radiographic data were collected. Results: Thirty four patients were identified for inclusion in the study. The average age was 64.35 years. All patients had ulcers at the time of surgery and no patient had re-ulceration of the involved digit postoperatively. 30/34 patients had hammertoe deformity preop. 22/34 (65%) had positive probe-to-bone and 19 of these had culture positive osteomyelitis. No patients had an MRI preoperatively. 79% of patients had positive bone cultures, 62% had positive pathology demonstrating osteomyelitis, and 100% had clean margins. Methicillin-resistant Staphylococcus epidermidis (MRSE) was the most common pathogen (32%). One patient required revision surgery with a repeat distal Symes amputation due to dorsal flap necrosis, but they went on to heal the revision surgery without incident. No patient required additional amputation related to the operative digit. The average followup was 29.53 months. Conclusion: In-office distal Symes lesser toe amputation is a safe, reliable, and cost-effective treatment for non-healing tip of lesser toe ulcers complicated by osteomyelitis. The procedure allows bone biopsy diagnosis, removes the non-healing ulcer, confirms clear margin regarding osteomyelitis, and addresses the underlying toe deformity to minimize the chance of re-ulceration.