One of the leading theories of social learning today is Wenger's theory of Communities of Practice' (CoP-theory). CoP-theory reiterates basic tenets of social learning theory yet it us set apart from other theories of social learning and education not only by centering on identity-formation but by positing four key dualities as inherent structural features of the educational process. While concurring with Wenger's 'dilemmatic' understanding of education and his open-ended, practice-based conception of identity-formation, we argue that Wenger's theory overlooks central elements that are needed in order to fully articulate the ends of the educational process, as he conceives them. We claim that further supplementation is needed to support the kind of educational processes that Wenger advocates. Referring to the work of Jack Mezirow and Charles Taylor, this supplementation concerns both critical (rational) reflection and 'ethical imagination'. Rather than threatening the coherency of the theory, we claim that these supplementations are internally derived from the ends of CoP-theory and are necessary for its very possibility. To remain in line with Wenger's dilemmatic structure of education, these supplementations are presented in the form of a duality: the tension between artistic and ethical imagination.