While scholars observe positive trends in sustainability education, sustainability education as a field still finds itself mired between institutional inertia and strong drivers for transitions (Jones et al., 2010). As Van der Leeuw et al. (2012, p. 118) describe: Academic institutions remain so inertial because the professoriate remains in familiar and comfortable patterns. This is human nature, but denudes the academy of the energy and passion needed for change. Following form, the next generation of academics learns the habits, practices, and methods of their professors, replicating the status quo. A more bilateral relationship between faculty and students might produce different outcomes. If students played an equal role in the development of curricula, selection of course content, and initiation of applied projects, how different might the impact of the academy become? The vision implicit in this description is of sustainability education defined by innovative, multilateral relationships among faculty, students and surrounding communities. This chapter presents work in progress at three educational sustainability programmes — one each in Canada, Germany and the United States of America — seeking to contribute to transformative change for sustainability by way of educating ‘sustainability change agents’ (Moore, 2005; Svanström et al., 2008).