We describe 10 patients with inverted papillomas (IPs), uncommon endophytic epithelial tumors that arose in the nose, paranasal sinuses, and lacrimal sac, that invaded the orbit; review the world literature on IP; and discuss treatment options. Patients ranged in age from 49 to 72 years (mean age, 62 years; median age, 66 years). Six patients were men and four were women. Presenting symptoms and signs included a medial canthal mass (n = 5), epiphora/lacrimal drainage obstruction (n = 3), inability to wear eyeglasses (n = 2), diplopia (n = 1), and painful dentures (n = 1). Histopathologic examination was performed in each patient and revealed all patients to have areas with malignant transformation: six patients with IPs that contained areas of squamous cell carcinoma and four with areas of transitional cell carcinoma in the tumor within the orbit. Eight of the patients with IPs had a recurrence after initial resection. In two patients, the IPs were completely excised and did not recur; yet, follow-up was short. Eight patients required orbital exenteration for local control of disease. Nevertheless, local spread of tumor through bone to brain occurred in three patients with orbital involvement. Indeed, IPs that invade the orbit have a high incidence of malignancy and are locally aggressive tumors. Treatment is difficult, and the recurrence rate is high. Early, wide excision of this aggressive tumor provides the best chance of cure.