Secondary complications in an anophthalmic socket can include late appearing shrinkage due to scarring and squamous cell carcinoma. This article reports a 51-year-old man who 27 years after an enucleation developed an inability to retain his ocular prosthesis due to an acquired multilobular fleshy mass in his inferior fornix. The patient had worn his prosthesis without removal for years at a time. Microscopic evaluation of the excised lesion disclosed a pseudoadenomatous (pseudoglandular) hyperplasia of the conjunctival epithelium with myriad goblet cells and accompanying chronic inflammation. In cross section, these structures microscopically resembled an adenoma but were found to display multifocal origins from the surface epithelium resembling exaggerated pseudoglands of Henle. Simple excision without recurrence 6 months later has permitted a new prosthesis to be comfortably worn with stability.