Medical literature offers no clear treatment guidelines when performing amputations for gangrene of the forefoot despite a high percentage that suffer poor outcome due to infection. Gas gangrene and wet gangrene are often preceded by dry stable gangrene. This is a retrospective review of consecutive patients who underwent forefoot amputation and bone biopsy as treatment of forefoot gangrene by a single surgeon. Procedures performed included digital, ray, or transmetatarsal amputation with bone biopsy sent for both culture and histopathologic evaluation. One hundred patients (35 females, 65 males) met inclusion criteria. Mean follow-up was 9.6 months. Mean age was 63.5 years old. Forty-six out of 100 (46%) had elective amputation while 54/100 (54%) were emergent for acute infection. Vascular intervention was performed in 52/100 (52%). Seventy-eight out of 100 (78%) had histopathologic diagnosis of acute osteomyelitis while 82/100 (82%) had positive bone culture. Patients with acute infection had worse outcomes, with higher rates of more proximal amputation and delayed wound healing. We found that 79.7% of patients who underwent forefoot amputation due to gangrene had underlying osteomyelitis. We also found that those with acute infection during the time of amputation had poorer postamputation outcomes such as delayed wound healing, revision surgery, and high rates of more proximal amputation. Therefore, it may imply that earlier amputation of stable gangrene prior to becoming acutely infected may decrease the occurrence of osteomyelitis and avoid some of the preventable postamputation complications. Further studies are warranted.