During a conference of pain specialists, some of the experts addressed the potential management of four prevalent but difficult painful conditions, namely, chronic postsurgical pain (CPSP), knee osteoarthritis, chest trauma, and facet joint arthropathy. In all cases, the conditions posed challenges in accurate diagnoses as well as safe, effective treatments, especially using locoregional blocks. It is not clear why some surgical patients develop CPSP and others do not, although some risk factors have been identified. More importantly, the transitional phase of pain from acute to chronic deserves greater scrutiny. It appears as if more aggressive and more effective perioperative and postoperative analgesia could help mitigate or possibly prevent CPSP. Knee osteoarthritis is prevalent but is often managed pharmacologically and then with joint replacement; many patients simply live with the condition which can be viewed as a disease of the entire joint. New approaches with intra-articular injections of hyaluronic acid, platelet-rich plasma, and botulinum toxin may provide safe, effective, and durable pain control. Chest trauma can be extremely painful and a source of morbidity, but its management tends to rely on watchful waiting and drug therapy. New approaches to regional nerve blocks can be beneficial and may reduce troublesome symptoms such as the inability to cough or clear the lungs. Facet joint arthropathy is very prevalent among older people but is not completely clarified. It may be the source of intense pain with limited management strategies. The role of nerve blocks in facet joint arthropathy is an important new addition to the armamentarium of pain management, particularly for geriatric patients.