Vaginal cuff dehiscence (VCD) is a rare but serious condition associated with high morbidity, especially in the presence of an evisceration. It usually occurs as a complication of hysterectomy, but has also been reported after other pelvic surgeries. In this article, we will present two cases of vaginal cuff dehiscence with evisceration in post-menopausal patients. Both cases occurred post-operatively, the first after a laparoscopic radical hysterectomy and the other after a trachelectomy performed by robotic-assisted laparoscopy (with a prior history of subtotal hysterectomy). Both cases were treated surgically, the first by a combined laparoscopic and vaginal approach, and the second case only by laparoscopic approach. The main risk and protective factors are discussed in a narrative literature review which summarizes the available evidence on this rare condition, discussed by type of study designs and thus evidence level. A laparoscopic vaginal cuff closure is the most protective factor in preventing VCD, compared to a vaginal closure. Clinicians should be aware of this condition and of its risk factors and precipitating events in order to identify high-risk patients. Knowledge of these allows prompt recognition, which is crucial for adequate management, for which multiple approaches have been described.