An 86-year-old male presented with a 2-year history of a gradually enlarging parotid mass. He denied any facial weakness, numbness, or pain. He was a nonsmoker and occasional alcohol user. The patient had no history of cutaneous malignancy. Examination revealed normal facial nerve function and a 1.5-cm firm, mobile left parotid mass. The remaining head and neck examination was significant for a firm, exophytic, friable mass at the left base of tongue (Figure 1) and a firm, enlarged left level III lymph node. Ultrasound of the parotid was performed, which showed a cystic 2.2 cm lesion with minimal solid components. Fine needle aspiration (FNA) of the parotid demonstrated clusters of epithelial cells and FNA of the level III neck was positive for poorly differentiated squamous cell carcinoma. Positron emission tomography scan showed an fluorodeoxyglucose (FDG)-avid left base of tongue tumor with increased avidity in the left neck levels II and III as well as the left parotid gland (Figure 2). The patient was taken to the operating room and underwent robot-assisted left base of tongue resection, left select neck dissection levels II to IV, and left superficial parotidectomy. The primary base of tongue tumor was a 3.1 cm grade 3 HPV-positive squamous cell carcinoma. Four of 39 lymph nodes in the neck were positive, the largest being 5 cm with extracapsular extension. Surgical margins were negative. Frozen section pathology of the superficial parotid gland was positive for metastatic squamous cell carcinoma. This finding prompted proceeding with total parotidectomy. Two of 7 intraparotid lymph nodes were positive, both in the superficial parotid. The patient recovered well and was treated with adjuvant proton radiotherapy. Salivary gland tumors represent 5% to 10% of tumors within the head and neck. 1 Of these, 80% arise from the parotid gland. 1 The ability of otolaryngologists to appropriately evaluate and treat parotid masses is vitally important. A broad differential diagnosis must always be considered. Masses of the parotid gland can represent both benign and malignant neoplasms, among other etiologies. Parotid gland neoplasms represent malignancy in 20% of cases, one quarter of which are metastasis from head and neck primary sites. 2,3 The parotid gland has unique embryologic development from ectodermal outpouchings, which encapsulate the mesoderm-derived lymphatic system. 2 This results in a wide lymphatic drainage basin