Diabetes-related tip of lesser toe ulcers have typically been associated with both 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. We report on a well-known, but poorly reported, technique for surgical management of non-healing tip of lesser toe ulcers. After approval by the institutional review board, a review was performed of consecutive patients who had undergone office-based distal Symes toe amputation for a non-healing tip of lesser toe ulcer from January 2007 to December 2012. A variety of clinical, laboratory, and radiographic data were collected. A total of 48 consecutive patients (48 toe ulcers) were identified for inclusion in the present study. All patients had ulcers at the time of surgery, and no patient developed repeat ulceration of the involved digit postoperatively. Of the 48 patients, 44 (92%) had hammertoe deformity preoperatively. Also, 30 patients (63%) had positive probe-to-bone results, and 29 (97%) of these patients had culture or histologic findings positive for osteomyelitis. Of the 48 patients (48 ulcers), 73% had positive bone cultures, 69% had positive pathologic findings demonstrating osteomyelitis, and 100% had clean margins. Methicillin-resistant Staphylococcus epidermidis was the most common pathogen isolated (13 of 48, 27%). No patient required additional amputation related to the operative digit. The mean follow-up period was 28.79 months. Our results have shown that in-office distal Symes lesser toe amputation is a safe, reliable, and likely cost-effective treatment of non-healing tip of lesser toe ulcers complicated by osteomyelitis. This office-based procedure allows bone biopsy diagnosis, removes the non-healing ulcer, confirms clear margins regarding the osteomyelitis, and addresses the underlying toe deformity to minimize the chances of repeat ulceration.