Anaplastic or malignant meningiomas that are classified as World Health Organization (WHO) grade III account for less than 1% of all meningiomas diagnosed. Despite the aggressive course, distant metastases are a rarity, occurring in only 0.1% to 0.2% of cases. We report the case of a 56-year-old woman who presented with parasagittal benign meningioma that underwent malignant transformation along with metastasis into the right orbitosphenoid region. The clinical, radiological, and histopathological aspects are highlighted, with an emphasis on the natural history of meningiomas.