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ABSTRACT Background: Multiparametric magnetic resonance imaging (mpMRI) is increasingly used for risk stratification and preoperative staging of prostate cancer. It remains unclear how Grade Group (GG) interacts with the ability of mpMRI to determine the presence of extraprostatic extension (EPE) on surgical pathology. Methods: A retrospective review of a robotic assisted laparoscopic radical prostatectomy (RALP) database from 2016-2020 was performed. Radiology mpMRI reports by multiple attending radiologists and without clear standardization or quality control were retrospectively assessed for EPE findings and compared with surgical pathology reports. The data were stratified by biopsy-based GG and a multivariable cluster analysis was performed to incorporate additional preoperative variables (age at diagnosis, PSA, etc.). Hazard ratios were calculated to determine how mpMRI findings and radiographic EPE relate to positive surgical margins. Results: Two hundred and eighty nine patients underwent at least one mpMRI prior to RALP. Preoperative mpMRI demonstrated sensitivity of 39.3% and specificity of 88.8% for pathological EPE and had a negative predictive value (NPV) of 49.5%, and positive predictive value (PPV) of 84.0%. Stratification of NPV by GG yielded the following values: GG 1-5 (49.5%), GG 3-5 (40.8%), GG 4-5 (43.4%), and GG 5 (30.4%). Additionally, positive EPE on preoperative mpMRI was associated with a significantly decreased risk of positive surgical margins (RR: 0.655; 95% CI: 0.557-0.771). Conclusions: NPV of prostate mpMRI for EPE may be decreased for higher grade tumors. A detailed reference reading and image quality optimization may improve performance. However, urologists should exercise caution in nerve sparing approaches in these patients.