Emergency physicians who are confronted with orbital injuries must recognize that the transorbital route offers little resistance to intracranial penetration. Neither direct inspection of an orbital wound nor plain radiographs are sufficient to evaluate the extent of penetration beyond the orbital confines. A high index of suspicion is critical to the proper assessment and subsequent management of such injuries. We present two cases of penetrating injury. In the first, an arrow caused a hematoma in the superior cerebellar peduncle after passing through the medial orbit and superior orbital fissure. In the second, a wire entered the upper lid, fractured the orbital roof, and caused a frontal hematoma.