Circumcision is a commonly performed operation. Regional analgesia is provided either by penile block or caudal block. Each approach to anesthetizing the penis has attendant risk and benefits. The provider has several decision points to observe when choosing which, if either, technique to apply. The basic anatomic factors (including the identification and significance of sacral dimples), technical steps, risks, and considerations of each are discussed. Overall, each block offers benefit to the patient, and choosing between them can be based on need for ambulation postoperatively, operator experience, and availability of appropriate equipment. When available, ultrasound can enhance the efficacy of penile nerve blocks.