Aims: To investigate 3 cases of chronic parotitis secondary to an acute bend in Stensen’s duct caused by an enlargement of the masseteric space. Results: Three female patients presented with symptoms consistent with obstructive parotitis including glandular swelling and tenderness during meals. A 10-year-old patient had unilateral facial swelling with enlargement of the masseter muscle and mandible later diagnosed as fibrous dysplasia. Salivary endoscopy showed an acute bend in Stensen’s duct secondary to a mass effect. The patient’s parotid swelling resolved following debulking of the mandibular mass and sialendoscopy with irrigation. Two adult patients with bilateral parotid involvement presented with bilateral masseteric hypertrophy and dental wear facets consistent with bruxism. Salivary endoscopy revealed bilateral kinking of Stensen’s duct with jaw closure. Both patients improved symptomatically following nightly bite guard use and ultrasound-guided Botox injections of the masseter muscle and parotid. Conclusion: Obstructive parotitis is rarely caused by an acute masseteric bend. Diagnosis of a kinking Stensen’s duct is aided with salivary endoscopy and imaging to determine the precipitating pathology. In the case of masseteric hypertrophy, symptomatic improvement can be achieved with Botox-induced atrophy of masseteric hypertrophy or with surgical reduction for associated fibrous dysplasia.