Cutaneous metastasis in thyroid carcinoma is extremely rare (<1%) and usually accompanies follicular and papillary thyroid carcinoma (PTC). Less than 20 cases of anaplastic thyroid carcinoma with cutaneous metastasis have been described so far. We present a case of a 53-year-old male who presented with a longstanding thyroid swelling with a history of rapid increase for 2 months associated with bilateral cervical lymphadenopathy. Fine needle aspiration cytology revealed a variable picture from both lobes of the thyroid with PTC in the left lobe and anaplastic carcinoma in the right lobe. Total thyroidectomy with bilateral modified radical neck dissection was performed which supported the cytology findings. BRAF V600E and PD-L1 expression were analyzed using immunohistochemistry. Postoperatively, the patient received radioactive iodine ablation therapy, but developed cutaneous metastasis in the neck and thoracic region, which on fine needle aspiration cytology revealed metastatic anaplastic thyroid carcinoma. The patient did not respond to the therapy and succumbed to the disease within a month after surgery. Cutaneous metastasis may develop in thyroid carcinoma, which must be differentiated from skin adnexal malignancies due to different management strategies. BRAF V600E and PD-L1 expression in primary thyroid tumors can identify the possible cases who may benefit from immunotherapy, which can lead to an improved overall survival.