For decades, Thailand has been at the forefront of sex reassignment surgeries. The neovagina created by recto-sigmoid vaginoplasty is much more complex procedure when compared with penile skin version technique, but yielded more satisfactory functional outcomes. We reported an unusual case of life-threatening small bowel obstruction following previously successful recto-sigmoid vaginoplasty in a transgender woman. Transgender individuals have unique healthcare needs. However, various gaps still exist to provide multi-disciplinary care for these patients. The rate of adhesive small bowel obstruction is highest in the early period of any intra-abdominal post-operative surgeries, but the risk remains life-long. Transgender women receiving complicated vaginoplasty should be instructed to continue long-term follow-up to ensure early detection and management of post-operative complications.