A 65-year-old diabetic female presented with a 3-week history of a left swollen foot after a minor inversion injury and was found to have a minimally displaced fibular fracture. Despite casting and strict instructions to remain non-weight bearing, the patient continued to bear weight and later developed a significantly more displaced fracture with a draining ulcer. This injury eventually required a tibiotalocalcaneal arthrodesis using a retrograde hindfoot nail. Neuropathy and neuropathic fractures can be devastating complications of diabetes and thus require early diagnosis and intervention because they may result in significant morbidity for the patient. Thorough assessment involving imaging, a complete history and physical examination, and tools such as a 129 Hz tuning fork and the 10 g Semmes-Weinstein monofilament are paramount to establishing an accurate initial diagnosis. These tactics aid in future follow-up of the patient's injury and can be employed in both the clinic and the emergency department. Although management remains controversial for neuropathic ankle fractures because both conservative and surgical treatment regimens have high complication rates, open reduction and internal fixation continues to be the treatment of choice once closed reduction has been attempted and fails. Education is essential because diabetic patients have compromised pain and pressure sensation, which can lead to injuries and subsequent complications of which they are simply unaware. Physicians must be diligent when evaluating the diabetic foot and be explicit when providing instructions to these patients because preventing these injuries and their complications is the best patient care available.