A difficult vaginal hysterectomy can challenge the most accomplished pelvic surgeon. Large uterine size or prior pelvic surgery is commonly thought to make a vaginal hysterectomy more difficult, but more common issues such as large body habitus or extensive prolapse may make performing a vaginal hysterectomy even more technically challenging. The knowledge and expertise needed to perform a routine vaginal hysterectomy are prerequisites for managing more difficult cases. As techniques in pelvic surgery continue to evolve, it is critical that this minimally invasive procedure continue to be taught and performed.