A case of a 64-year-old woman is reported, who developed new-onset pain over a preexisting area of right mandibular fullness. Clinical examination, MRI, and fine-needle aspiration cytology confirmed the diagnosis of a benign parotid gland tumor-pleomorphic adenoma, which was treated by total parotidectomy with complete removal of the tumor. When evaluating a patient with orofacial pain, oral health care providers should be cognizant of all potential differential diagnoses, especially in the setting of red flags such as persistent or enlarging facial swelling/fullness.