Regional analgesia is an important adjunct for perioperative pain management in the setting of pediatric penile surgeries. Caudal epidural analgesia (CEA) is the most common analgesic technique performed, but it has limitations and associated morbidity. The pudendal nerve block (PNB) is an effective alternative to CEA with a lower risk profile; in prior examination of the approach, PNB has been demonstrated to have similar postoperative pain control outcomes. We describe our technique and highlight observations made as we have transitioned from CEA to PNB for many patients.