The art of diagnosis consists in the recognition of signs and symptoms and their interpretation under the light of individual circumstances obtained from the patient's history. In medicine we encounter cases that are straightforward and cases that are complex as they are the result of a rare disease or of uncommon presentation of a common disorder. We present in this paper the case of a patient with a non-healing traumatic wound to her shin, which after unsuccessful treatments was biopsied and an unexpected diagnosis of necrobiosis lipoidica diabeticorum was made. This led to the institution of disease-targeted wound care leading to complete resolution in a short period of time.