It is commonly assumed that to educate means to control or guide a person's acting and development. On the other hand, it is often presupposed that the addressees of education must be seen as being endowed with free will. The question raised in this paper is whether these two assumptions are compatible. It might seem that if the learner is free in her will, she cannot be educated; however, if she is successfully educated, then it is doubtful whether she can be seen as free. Inspired by the current philosophical debate on the compatibility of free will and determinism, this paper spells out two versions of this dilemma. The first version relies on the idea that to be free means being the causal source of one's actions. The second formulation refers to the notion of freedom as the ability to act otherwise than the way one actually acts. The solution to the dilemma that is developed in this paper, however, uses a third concept of free will—to be free means being able to act on reasons.