23 Background: Prostate cancer (PCa) is the second-most diagnosed cancer and the second leading cause of cancer deaths in United States Males. Due to an emphasis on early detection of PCa, only a small percentage present with distant disease. We report cases of ocular metastasis of PCa, a late finding of PCa. Methods: Systematic review of the literature and pooled analysis of published cases of PCa with optic canal or orbital metastasis, including one from our institution. A subgroup analysis compared those who presented with optic metastases as their initial presentation (IP) versus those who presented with optic metastases after diagnosis (AD). Results: 39 patients with ocular metastasis of PCa were selected for this study. Twenty-one cases (53%) presented with ocular metastasis in the initial presentation, and 18 presented with an optic canal metastasis after diagnosis. The overall average age was 66 years (45-85 years). The average age for the IP group was 70 years (59-85 years) and 62 years (45-70 years) for the AD group. Metastatic sites varied between cases. Nineteen cases (49%) presented with widespread lesions involving the axial skeleton, with 8 IP cases (44%) versus 11 AD cases (52%). Ten cases (26%) involved solitary metastases to the optic nerve, optic disc, choroid, or orbit, with 5 IP cases (2%) versus 5 AD cases (24%). Three cases (7.5%) presented with bilateral orbital metastases. One case (2.5%) involved bilateral solitary lesions to the optic nerves. The common complaints patients presented with were proptosis (33%), diplopia (26%), decreased visual acuity (41%), and vision loss (10.3%). Thirty-seven cases reported primary adenocarcinoma on histology (95%). Thirty cases reported mortality data, with 16 reporting patient death after diagnosis. Of these, 6 cases (out of 12) report death from PCa in the IP group, and 10 cases (out of 18) report death from PCa in the AD group. Conclusions: Despite early prostate cancer screening increases, patients can present with distant metastasis as their initial presentation. We recommend prompt tumor molecular/genetic testing to inform targeted treatment when faced with atypical cases.