Solitary fibrous tumor of the orbit is a rare neoplasm that often follows a benign course. Additional involvement beyond the orbit is even rarer, having only been reported in 2 cases previously. The authors describe a 62-year-old patient with a primarily intracranial lesion including orbital extension which was debulked and initially diagnosed as meningioma. Two recurrences 3 and 4 years later disclosed a solitary fibrous tumor, with the initial histopathology being revised to the same diagnosis. This rare presentation of an orbital solitary fibrous tumor highlights the surgical challenge faced when the tumor straddles the cranio-orbital junction and demonstrates the potential for rapid regrowth after incomplete excision.