Positive surgical margins represents incomplete resection by the surgeon, and the elimination of positive margins represents the only clinical feature during radical prostatectomy that can lead directly to improved cancer outcomes. The introduction of new robot-assisted technology and technical refinements has led to declines of positive surgical margins. Although margins induced by incomplete cancer resection by the surgeon have been reduced for organ-confined disease, the 'Holy Grail' of zero margins is not yet attainable in prostatectomy, and is more problematic in cancer that has penetrated beyond the prostate. Intraoperative frozen biopsies are imprecise. The union of real-time optical coherence tomography technology of the da Vinci robotic platform for identification of positive margin sites, and technical advances with wider excisions during surgery may provide promise for further reduction of surgical margins to zero.