Vaginal pessaries are routinely used for initial management of pelvic organ prolapse and for women who are poor surgical candidates. Serious complications of long-term use without routine follow-up include erosion into surrounding organs and the development of fistulas. It is unclear however, if long-term use and chronic irritation could potentially contribute to development or delay the diagnosis of vaginal or cervical cancers. A 72-year-old Caucasian woman with a vaginal pessary retained for 3 years, who presented with leukocytosis and coagulopathy, was discovered to have stage II vaginal adenosquamous carcinoma upon surgical pessary removal. Chronic irritation and lack of follow-up with pessary use may contribute to masking the development and delaying the diagnosis of vaginal cancer in women with risk factors. Pessary use requires frequent follow-up to prevent complications.