A 63-year-old woman presented subacutely with signs of orbital apex and cavernous sinus disease in the setting of widespread, untreated metastatic carcinoma of the uterus. MRI revealed a destructive lesion of the left sphenoid wing with compression of the orbital apex and with possible extension in the cavernous sinus. The underlying diagnosis was confirmed with repeat endometrial biopsy, revealing well-differentiated endometrial adenocarcinoma. Given the supporting clinical evidence for metastatic disease and the radiologic characteristics of the lesion, the decision was made to not perform a confirming orbital biopsy.