A previously healthy 35-year-old man experiencing slowly progressive, painless proptosis of the right eye. Visual function was normal, but supraduction was limited. Computed tomography revealed a superior, extraconal orbital mass. Subtotal excision was performed, and a diagnosis of liposarcoma was rendered only with expert analysis. Despite subsequent orbital exenteration and postoperative radiation, a local recurrence developed 5 years later. The clinical features that predict recurrence, and management options that may promote longevity, are discussed.