Abstract Intracranial mass lesions can lead to transtentorial uncal herniation, and pupillary asymmetry is a well-recognized sign of impending cerebral herniation. Impending uncal herniation can lead to ipsilateral, bilateral, or uncommonly the contralateral pupillary dilatation. We report a case of a 22-year old, who had contralateral pupillary dilatation due to expanding intracranial mass lesion and recovered well after neurosurgical intervention. This case illustrates contralateral pupillary dilatation (“false-localizing” sign) in a sub-group of patients, and if untreated and ICP continues to rise, this is followed by ipsilateral pupil dilatation.