Dural metastases from advanced prostate cancer are considered an uncommon diagnosis. However, autopsy studies show a high association between advanced prostate cancer and metastases to the meninges. Because the overall survival of advanced prostate cancer patients is expected to improve with the advent of new therapies, the incidence of clinically relevant dural metastases from prostate cancer will likely increase. We present a case of a heavily pre-treated castration-resistant prostate cancer patient who developed metastases to the duramater. This entity should be considered in the differential diagnosis of any patient with advanced castration-resistant prostate cancer and neurological symptoms. Clinicians should also be aware of the poor prognosis and survival rates associated with the condition.