Trichobezoars are indigestible masses of ingested hair commonly found in the stomach, often presenting with symptoms related to gastric outlet obstruction and severity related to the mass's size and location. Gastrointestinal complications include ulceration, perforation, peritonitis, pancreatitis, obstructive jaundice, pneumatosis intestinalis, and intussusception. Management of trichobezoars differs from that of other forms of bezoars, which can often be addressed with chemical dissolution. Trichobezoars are highdensity structures that are also resistant to enzymatic and pharmacotherapy degradation, and as such, they require endoscopic, or more commonly, surgical removal. Here, we present the diagnosis and surgical management of a 12-year-old female with a large trichobezoar causing gastric outlet obstruction, with an associated Rapunzel syndrome manifesting as multiple small intestinal intussusceptions.