This essay applies lessons from John Dewey's theory of democracy and democratic education to the modern development of information communications technologies and the assertion that the development of such technologies will lead to a more open, more democratic society. Given the continuity of the technology and its applications with structures of oppression within modern society, any attempt to resolve or democratize technology through skills-based training is bound to fail, as this does not resolve the cultural habits that enable oppression through technology. To this end, what is necessary is democratic education that recognizes the unique contexts in which students become individuals and furnishes flexible habits of transaction.