Cesarean section is the most common surgical procedure performed in the world. Postoperative pain management remains a challenge, particularly in a context of enhanced recovery after surgery. Several barriers related to the specific condition of 'postpartum recovery' may prevent application of effective analgesia in this population. The present review focuses on novel approaches of cesarean section postoperative pain assessment, beyond pain-rating intensity, including objective patient-centered recovery parameters. Predictive tools currently available to target patients at high risk of acute and chronic pain are also examined. Postoperative pain after cesarean section is more severe than reported in the majority of randomized control trials. Pain seriously interferes with early and also late functional recovery, although Enhanced Recovery after Surgery (ERAS) programmes are being promoted. Pain-rating scores can differ from scores of physical comfort and physical independence, which are priorities for postpartum patients. Further, the value of subjective pain intensity rating to adapt analgesic prescription is misleading and may promote opioid over-prescription. Available tools to predict at-risk patients for severe pain after cesarean section are not easy to use in daily clinical practice and have, at best, moderate predictive value. Patient and healthcare provider education on reported pain and well tolerated analgesic use is the key to improve postpartum pain management after cesarean section.