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Sigmoid volvulus (SV) is a rare cause of intestinal obstruction in children. Its varied presentation and rapid progression engender a high risk of morbidity and mortality. We report two cases of SV in teenage boys. Patient 1 is 16 years old and patient 2 is 17. Both presented to our institution with recent-onset abdominal pain, constipation, and nausea and vomiting, and both had previous episodes of SV. Patient 1 had been surgically treated with manual derotation, and patient 2, who had redundant colon, had two past episodes of endoscopically-treated SV. Both patients were in poor condition and had distended but treatable abdomens, with no peritoneal signs. After computed tomography (CT) confirmation of the clinical impression of no ischemia or perforation, we decided to attempt detorsion of the SV and decompression of roximal dilated colon by flexible endoscopy, and planned for elective surgery shortly after the endoscopic procedure. Because sigmoid volvulus is so rare in children, operative and technical details of endoscopic management are gleaned from the larger adult experience. In patients without signs of complication, initial endoscopic reduction is the gold standard, and elective sigmoid resection with primary anastomosis is often required to prevent recurrence.