Neuraxial anesthesia is often challenging in patients with obesity, spinal deformity, prior spinal surgery, ankylosing spondylitis, or of advanced age, as conventional landmark-based techniques frequently fail in this population. Ultrasound guidance has improved puncture accuracy; however, commonly used approaches may still be limited by patient positioning and the side from which the operator prefers to work. We report five cases of extremely difficult neuraxial anesthesia in which the procedure was successfully performed using an ultrasound-guided paramedian sagittal long-axis out-of-plane approach. This technique allows continuous visualization of the lamina and the anterior–posterior complex, providing a short and direct puncture path with real-time guidance. All procedures were completed successfully on the first attempt, with short puncture times and no anesthesia-related complications. These cases suggest that the ultrasound-guided long-axis out-of-plane approach is a safe, effective, and flexible option for managing difficult neuraxial anesthesia.