Digital Papillary Adenocarcinoma (DPA) is a very rare neoplasm of sweat glands, with approximately 100 cases in the literature. We present a rare case of DPA of the ankle in a 66-year-old African American man. DPA has a high potential for metastases to the lung and lymph nodes, and initial treatment often entails wide excision or complete digital amputation. DPA typically presents as a painless lesion or mass of the distal digits of the hands or feet. With the limited available literature regarding this malignancy, there is no standard approach to treatment. Wide excisional margins with sentinel lymph node mapping and biopsy are based on extrapolation for other tumors. In the following report, we discuss a representative case and the current literature on the presentation, treatment and pathology of this rare neoplasm.