Anaplastic thyroid carcinoma (ATC) is an extremely rare but aggressive form of thyroid cancer. Although local tissue invasion is characteristic of this disease, systemic metastases are a common clinical finding. Our case discusses an unusual presentation of cutaneous metastases to the scalp in a patient with a remote history of ATC. It also highlights the utility of immunohistochemical staining in determining the origin of a tumor when the source of primary malignancy is not readily identifiable.