A 46-year-old man with a history of right orbital fractures and blindness underwent simultaneous fracture repair and enucleation with orbital implantation. During surgery, an orbital catheter was placed for administering local anesthesia to control postoperative pain. After administration of local anesthesia through the catheter on postoperative day 1, the patient had development of a complete ptosis, total ophthalmoplegia, mydriasis, vision loss from 20/20 to NLP, and hypesthesia of the V1 and V2 trigeminal nerve distribution. Intraocular pressures and dilated funduscopic examination were normal. There was no evidence of central nervous system effects or respiratory depression. After 4 hours of observation, the vision, sensation, motility, ptosis, and pupil response all returned to normal. Although rare, contralateral cavernous sinus/orbital apex syndrome may occur with indwelling orbital catheter administration of local anesthetic in an orbit with fractures.