The use of captopril has been linked to scarce adverse events characterized by parotid glands enlargement. We report a case of captopril-induced parotid enlargement in a patient with uncontrolled hypertension. A 57-year-old male presented to the emergency department (ED) with an acute state of headache. The patient has a background of untreated hypertension for which he was managed in the emergency department (ED) by the administration of captopril 12.5 mg sublingually to control his blood pressure. Shortly after the drug administration, he started to experience bilateral painless enlargement of parotid glands that resolved a few hours after the drug was withdrawn.