Abstract There are three kinds of transfer: from prior knowledge to learning, from learning to new learning, and from learning to application. The central thesis of this chapter is that all three should start from the dilemmas or paradoxes learners may have when trying to reach transfer. Six of these are described. They are finding relevant prior knowledge; the paradox of tacit knowledge; using relevant prior knowledge while learning; recognizing relevant situations and conditions; the paradox of near transfer and far transfer; and the paradoxical “what” of transfer, including learning to learn. In order to optimize transfer one needs to help learners solve the problems they encounter and to find ways out of the various dilemmas and paradoxes. For the three kinds of transfer exemplary studies are described that illustrate the kinds of solutions developed and their effectiveness.