Papillary thyroid carcinoma, the most common subtype of thyroid malignancy, rarely presents with cutaneous metastatic spread. Despite metastatic cutaneous lesions presenting as slow and indolent growing nodules of the head and neck, such lesions most frequently appear in the setting of diffuse and dramatic metastatic disease and a bleak prognosis. Given the rarity of these metastatic lesions, the diagnosis may be delayed, and often the initial diagnosis is incorrect. Several case reports have been published in the literature noting unusual or interesting presentations of thyroid carcinoma with cutaneous metastasis. Here we present a classic case of a patient with a prior diagnosis of thyroid carcinoma presenting with a slowly growing ulcerated lesion on the neck nine years after partial thyroidectomy and characteristic histopathology on microscopic examination. Furthermore we review the literature regarding papillary thyroid carcinoma with cutaneous metastasis and the diagnostic challenge these lesions present to practitioners.