In the following work I want to ask some troubling questions about the concept of freedom in anarchist thought: what sort of freedom might we expect, once we are free from the state? How will anarchists maintain order, without denying certain freedoms? My first claim will be simply that these questions, crucial though they are to the anarchist project, remain largely unanswered. But I want tofocus primarily on a perhaps greater challenge — a challenge that most anarchists do not appear to have considered.