Superior orbital fissure syndrome (SOFS) is a rare disease. So when a case of this came at Aravind Eye Institute, a detailed case report was prepared to publish. A 56 years old male patient, a known case of prostatic malignancy with skeletal metastasis presented with ptosis, exotropia, diminished pupillary reflex and limitations in extraocular movements of left eye. MRI brain revealed diffuse skull base and leptomeningeal metastasis. Whole body CT scan showed metastasis in ribs, scapula and in pelvic bones. He was diagnosed to have superior orbital fissure syndrome due to metastatic prostatic malignancy and was offered steroids and radiotherapy.