Background: Leptomeningeal metastasis (LM) is a rare complication of prostate cancer (PCa) that involves spread of malignant disease to the meninges and carries a poor prognosis. This review aimed to assess the clinical findings, treatments, and outcomes of LM cases reported in the literature. Methods: We performed a literature search for case reports in PubMed, Scopus, and ScienceDirect from database inception to June 2022 using keywords “leptomeningeal carcinomatosis AND prostate cancer” and “leptomeningeal metastases AND prostate cancer.” The reference lists of previously published reviews were also searched to identify additional articles. Results: We included 41 patients with a mean age (±SD, range) at diagnosis of 67.5 (8.4, 46-87) years. The most common presenting symptoms were headache (32%), leg weakness (24%), nausea (22%), vomiting (20%), vision complaints (17%), sensory abnormalities (17%), back pain (12%), and confusion (12%). The median time from initial PCa to LM diagnosis was 36 months (range 0-252) and was reported in 37 patients (90%). The median time of survival from LM to death was 1.7 months (range 4 days – 14 months) and was reported in 28 patients (68%). Four patients (13%) were still alive when the reports were written, including one who was alive at 16 months and another at 252 months. The median serum PSA (±SD, range) at time of diagnosis was 137.5 (507.9, 3.1-1500) ng/mL. The most common diagnostic tests were a combination of neuroimaging and CSF analysis (41%), neuroimaging only (32%), and autopsy only (12%). The most common imaging modalities used to aid diagnosis were MRI (65%) and CT (32%). CSF cytology was positive for malignant cells in 55% of 22 cases (54%) that reported cytology results. Thirty-four cases (83%) reported treatments, and the most common treatments were radiation (56%), steroids (32%), surgery (26%), hormonal therapy (21%), and chemotherapy (21%). Conclusions: LM is expected to become more prevalent with the overall increasing incidence of PCa with therapeutic advancements, yet it remains difficult to diagnose and treat. The findings of this review suggest that neurological symptoms in patients with advanced PCa should prompt providers to obtain neuroimaging to investigate possible LM.