Primary cutaneous adnexal neoplasms are mostly benign in nature; however, there have been reports of malignant adnexal tumors with distant metastasis to lymph nodes. Adnexal cutaneous malignancy with metastasis to the gastrointestinal tract has never been reported. Here, we present a rare case of a man with primary adnexal cutaneous adenocarcinoma who presented with symptomatic anemia secondary to occult gastrointestinal bleeding, found to be from gastrointestinal metastasis of the adnexal malignancy.