We report 2 cases of pediatric hypopharyngeal perforation that occurred during endoscopy and 1 case of esophageal perforation that developed during nasogastric tube insertion at a tertiary care academic medical center. These cases were identified during a retrospective chart review. All 3 patients were treated with intravenous antibiotics and nasogastric tube feedings, and none experienced further sequelae. Perforations of the hypopharynx and esophagus in children during endoscopy or insertion of endotracheal and nasogastric tubes are not uncommon. Many affected children can be managed conservatively without surgical drainage, depending on the cause and specific location of the perforation and the timing of the diagnosis. We discuss the clinical criteria for various management options, and we offer an algorithm that outlines important clinical considerations in the decision-making process. Our aim in presenting these cases is to increase awareness of the management options for children with hypopharyngeal and esophageal perforations and to demonstrate the effectiveness of nonsurgical management in selected cases.