Anaplastic Carcinoma of thyroid is a very rare form of thyroid malignancy and exhibits markedly aggressive nature. The mean survival rate for patients with anaplastic carcinoma of thyroid is less than 6 months. Due to its poor prognosis and aggressive nature of the tumour, we report a case of a 52 year female with complaints of midline neck swelling since 1 year along with dysphagia. Computed tomography of neck revealed abnormal enhancing complex and heterogenous solid cystic lesion in the right lobe of the thyroid. Fine needle aspiration was suggestive of Lymphocytic thyroiditis with few atypical cells. Right Hemithyroidectomy was performed and histopathology suggested Anaplastic Carcinoma: lymphoepithelioma like variant with focal Insular carcinoma component with lymph node metastasis.