The distinction between “surface freedom” and “deeper freedom”, and thus between “surface problem of free will” and “deeper problem of free will”, is made by some philosophers of action in the contemporary study of free will. By appealing to this distinction, especially through an understanding of the problem of free will in the deeper sense, some philosophers made progress in solving the problem of free will in the naturalist direction. It is remarkable that on the basis of a reflection on Davidson’s model, Frankfurt takes “higher-order motivation” to be the key to solve the deeper problem, and Velleman further develops an epistemological solution to the problem. However, the epistemological solution has its own problems. Reflections of the problems suggest that teleological considerations may be needed for a solution to the deeper problem of free will.