Uterine inversion may be puerperal or non-puerperal. Puerperal uterine inversion is a rare obstetrics complication, with an estimated incidence of 1 in 30,000 deliveries. The occurrence of non-puerperal uterine inversion is even rarer such that there is no good estimate of its incidence. It is challenging to make the diagnosis of non-puerperal uterine inversion and a high index of suspicion needs to be present. Malignancy is an uncommon cause for non-puerperal uterine inversion, but it is important to keep it in mind so as to counsel patients appropriately and prevent repeat surgery wherever possible. There are also unique complexities in the assessment of a virgo intacta patient which needs to be overcome through the use of different approaches in physical examination and imaging. In this case report, there is a unique interplay of multiple complicating factors in a virgo intacta patient presenting with abnormal uterine bleeding secondary to a malignant fibroid polyp that had prolapsed out of the vagina causing uterine inversion. She eventually required two open surgeries in the management of her condition.