Regional spinal and epidural anesthesia are used commonly in operative procedures. While the most frequent complication, postdural puncture headache (PDPH), is a clinically diagnosed positional headache that is usually self-limited, subdural hemorrhage (SDH) is a potentially fatal complication that cannot be missed. We report a case of an otherwise healthy female who presented with persistent positional headache and was ultimately found to have a large subdural hematoma with midline shift requiring surgical evacuation.