Bezoars have different compositions and can be subdivided into trichobezoar, phytobezoar, pharmacobezoar, lactobezoar and food bolus. The reported incidence of bezoar is 0.4% with phytobezoar being the commonest. Rapunzel syndrome is an extremely rare complication when trichobezoar crosses the pylorus to enter the duodenum, ileum and colon. We present the case of a 29-year-old female with a oneweek history of abdominal pain, anorexia, nausea, vomiting, constipation, lethargy and a one-year history of increasing abdominal mass. Physical examination revealed a 20 cm palpable mass extending from the left upper quadrant to the umbilicus. Laboratory investigations demonstrated iron deficiency anemia and CT showed two well-defined foci within the gastric lumen consistent with trichobezoars. She was managed conservatively during her hospital stay and discharged home with a plan for elective laparotomy. We present this case to discuss the management of trichobezoars and to highlight the importance of early recognition of recurrence to avoid severe complications.