Chopart's amputation is a limb length-preserving amputation that retains function but often suffers from stump ulcerations. We report a case of a 68-year-old male patient with poorly controlled type 2 diabetes mellitus and peripheral arterial disease who underwent left Chopart's amputation, presenting subsequently with nonhealing ulcers at the Chopart stump and heel for >1 year. Total contact casting was initiated, resulting in rapid wound healing without further interventions. This case highlights total contact casting's effectiveness in managing ulcerations post-Chopart's amputation, potentially preventing revision amputations, and extending its usefulness to complex foot anatomy in patients with diabetes and peripheral arterial disease.