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So long as the environments of our educational institutions continue to embody the hierarchical and authoritarian structures that barricade certain forms of knowledge, our classrooms will continue to be limited spaces where our efforts at liberatory practices are frustrated. In this paper, Bisignani argues that liberatory pedagogy, when confined to the classroom, remains limited for both students and instructors whose goal is to engage students in working toward greater social justice. She describes the activist-apprentice model of service-learning undertaken with an introductory women’s studies students, situating this model within a recent history of radical educational experiments that sought to transgress both the physical and intellectual boundaries of the academy and to provide students with practical organizing and activist skills they can use in their own communities. More specifically, Bisignani will initially discuss some of the challenges that both students and instructors face in attempting to engage with critical pedagogy and service-learning within the confines of the academy. Then, by situating service-learning within an historical context of other radical educational experiments, she argues for the transformative potential of constructing countersites beyond university walls. Political philosophies regarding intentional exodus can help instructors to better theorize how their service-learning projects engage their students with available infrastructures and tools of resistance at these countersites. Finally, building on current feminist service-learning praxis as well as anarchist theories of education, she proposes an activist-apprentice model of service-learning and describe the project she undertook with her introductory women’s studies students. While traditional service-learning projects often have students volunteer with members from underprivileged groups in the community, activist-apprentice pedagogy pairs students with experienced organizers. This relationship not only fosters students’ critical awareness of the structural roots of injustice (theory), giving them set of skills that they then apply in their own endeavors to create change (praxis), but also provides students with a site outside the academy in which to practice these skills under the guidance of a mentor.