The following is a case report involving a 16 year old female with trichotillomania as an antecedent. This patient presented to the Emergency Room with a chief complaint of early satiety and persistent abdominal pain for the past 3 months. However, recently her abdominal pain has worsened and it is now complicated by nausea and vomiting. The physical exam was notable for epigastric pain on deep palpation. The biochemical analysis and abdominal ultrasound were otherwise unremarkable. An esophagogastroduodenoscopy was subsequently performed where a trichobezoar was discovered. It extended from the gastric fundus to the third portion of the duodenum. A surgical extraction of the trichobezoar was then performed. The trichobezoar was found to be 130 cm in length and 8 cm wide at its most cephalad aspect. It is important to note that they also found five mall perforations throughout the duodenum and jejunum. The patient was discharged with outpatient follow up with psychiatry. In this report we describe the case of a patient with Rapunzel syndrome that was complicated by small bowel perforation and we provide a review of the salient literature concerning this syndrome and its associated complications.