This is a question about the role of education. I wonder how far is education away from institutionalization? Sometimes teachers think they are helping their students to gain the ability of being free, while in fact they are putting their students into prison by telling them what is the content of freedom. Hope this was not a vague question. And if I am very interested in this question, whose works you recommend to read?
I'm not sure why you think a teacher would put his or her students into prison by telling them the content of freedom. My puzzlement is this: Isn't the question of whether or not I am free or in prison an objective fact about me and my life? It may well be that a teacher can lead a student to recognize (perhaps for the very first time) just how constrained and unfree the student really is. But that is not the same as actually creating the constraints. In fact, I am inclined to think that the more we know about the limits on our freedom, the better equipped we will be to moderate or eliminate our limitations. Perhaps still the most important philosopher of education, especially in regard to the kind of question you are asking, is John Dewey.