Rapunzel syndrome is a rare condition that occurs when gastric trichobezoar extends beyond the pylorus and into the bowel. Recurrent Rapunzel syndrome is an extremely rare entity, with only two cases reported in the literature so far. Here, we present a case of recurrent Rapunzel syndrome in a 15-year-old girl. She underwent laparotomy twice in five years to extract trichobezoars measuring 58 cm and 62 cm. In both stances when Rapunzel syndrome was diagnosed, a tuft of hair extending from the stomach toward the jejunum was observed. The patient underwent psychiatric consultation and supervision after the first laparotomy; however, a lack of follow-up resulted in recurrence. We conclude that complete removal of trichobezoar and psychiatric consultation, coupled with long-term follow-up, are essential to prevent recurrence.