Solitary fibrous tumor (SFT) is a rare neoplasm that is thought to be of mesenchymal origin. Occurrence of such a tumor in the orbit is rare, more so in its malignant form. Histopathologically, it can mimic several other tumors of the orbit and can be differentiated by CD34 positivity. We report a case of malignant transformation of an SFT of the orbit that recurred after 15 years. The differentiating histopathological features with special stress on the importance of CD34 positivity and principles of management are outlined. The need for long-term follow-up to detect recurrence and malignancy is stressed.