In this article, the author describes the liberatory and critical classroom she tried to create with preservice teachers. She reflects on how the perceptions of her teaching and of her class by one student led him to feel silenced inside the classroom but liberated to express his views of the community in e-mail dialogues. Anthony's actions in class--failing to come prepared to class, coming late to class, making derogatory statements toward other students--which disrupted the feelings of safety and community for many class members, contrasted starkly with the well-articulated expressions of oppression written in his e-mail. The article includes some of their written dialogue, which led to a self-study of the author's teaching practices and the boundaries of safety that she attempted to establish. In listening to Anthony's voice, the author discovered the need for shared risk taking, constant reflection, and open dialogue with her students.