We report the cases of an 89-year-old woman and a 77-year-old woman with long-standing chronic sialadenitis (60 and 10 years, respectively) who were referred to our large academic medical center for sialendoscopy. Both patients presented with symptoms of acute parotid duct obstruction in the background of long-standing parotid duct disease. Imaging demonstrated ductal dilation and periductal inflammation and, along with the clinical findings, was supportive of a diagnosis of acute parotitis in the setting of chronic obstructive parotid disease. Both patients underwent sialendoscopy. Intraoperative findings suggested the presence of a mass lesion in both cases, and biopsy confirmed a buccal space malignancy in each. Although benign processes such as ductal strictures and sialolithiasis are frequent causes of parotid duct system complaints, the possibility of a malignancy should be entertained and ruled out. Even in patients who have long-standing obstructive parotid symptoms, malignancy can be encountered as a new diagnosis. We discuss the unique presentation, workup, and management of our 2 patients, and we briefly review the current literature.