Pleomorphic adenoma is the most common neoplasm of the parotid gland, generally presenting as a slowly enlarging, firm, well-circumscribed, painless nodule. Occasional cases have presented after a short period of rapid growth or have been associated with pain. The vast majority of these tumors are solid, but rare examples have been associated with cystic degeneration or hemorrhage. Spontaneous and tumor-associated infarction of the parotid has been reported, but these examples have been limited to infarctions of Warthin's tumors and postoperative infarctions of salivary glands. We present the case of a 48-year-old male with a one-year history of a painful, enlarging, left parotid mass associated with paresthesia of the tongue. Computed tomographic examination of the parotid demonstrated a left superficial lobe mass with a rim of enhancement and low attenuation center. Fine needle aspiration yielded necrotic debris and atypical squamous elements that were thought to be compatible with carcinoma. A superficial parotidectomy with intraoperative frozen section revealed a pleomorphic adenoma with extensive central necrosis. To our knowledge, this represents the first reported case of an infarcted pleomorphic adenoma and illustrates the potential for misinterpretation of these cytologic and radiologic findings as indicative of malignancy.