To state the conclusion first, whether Subcision is a difficult treatment depends greatly on how deeply the anesthesia takes effect. The pain is not caused simply by the needle passing through the skin. A sharp pain occurs when the needle tip touches a layer that has not been anesthetized. Because the target is the bundle of fibers beneath the dermis that holds the depression down, applying only cream-type topical anesthesia to the surface will not eliminate sensation at that depth.
Rather than asking, “Does it hurt?”, asking, “What type of anesthesia will be used, and how deeply will it take effect?” is likely to produce a much more informative answer. The former tends to lead to a discussion of individual sensitivity and pain tolerance, while the latter asks about the design of the procedure itself.