This case involves a patient who presented to the hospital with complaints of dizziness, numbness to the fingertips and face, and shortness of breath. A CT without contrast revealed a large non-specific oval-shaped mass centered in the region of the left petrous bone with associated bone erosion. Radiological reports stated that the lesion was suspicious for chondrosarcoma. A further CT angiography demonstrated a non-enhancing hyperdense extra-axial mass with the left middle cranial fossa. During the procedure, venography was performed in an attempt to diagnose the venous drainage of the lesion but this step was met with some difficulty in passing the dye contrast. The pressure of the dye injection device was increased to facilitate adequate flow. The images show severe extravasation of dye contrast into the surrounding brain parenchyma and the physical exam of the patient showed blown pupils.