Information systems researchers that apply critical social perspectives frequently emphasize the potential for information technology to serve as a mechanism for increased rationalization, domination, and control. Such theorists often overlook or discount the liberating aspects of information systems. In this study, we apply the ideal of rational discourse developed by Jrgen Habermas to the phenomenon of Wikipedia in an effort to explore empirically the emancipatory potential of information systems. We contend that Wikipedia embodies an approximation of the necessary conditions for rational discourse. While several challenges persist, the example of Wikipedia illustrates the positive potential of information systems in supporting the emergence of more emancipatory forms of communication. The corresponding implications for researchers and design professionals alike are discussed.