Verrucous carcinoma of the endometrium is an exceedingly rare disease with only a few cases reported in the literature. We describe the case of a 68-year-old postmenopausal patient who presented with vaginal discharge. PAP smears were repeatedly reported negative and an endometrial curettage 2 years prior to the diagnosis only showed fragments of benign squamous epithelium. Because of continuous symptoms a hysterectomy was performed and revealed extensive squamous metaplasia of the endometrium with focal transition to verrucous carcinoma. This case demonstrates that benign appearing squamous epithelium in curettage specimens, especially when abundant, is not necessarily ordinary portio epithelium. In this setting, the clinical presentation becomes paramount for considering a well differentiated squamous carcinoma of the endometrium and avoiding diagnostic delay.