Despite the fact that John Dewey had a great deal to say about education and technology, many of his insights have yet to be understood or appropriated. A close reading of Democracy and Education offers support for the view that Dewey was prescient in proposing a pedagogy that was friendly to current initiatives in innovative classroom technology including inverted or “flipped” classroom projects in the United States and elsewhere and the Future Classroom Lab project of the European Schoolnet. In both of these initiatives application of tools and techniques grow out of educational occupations guided by teachers rather than being imposed on learning situations a priori. Both initiatives honor the pillars of Dewey’s educational philosophy as presented in his 1916 Democracy and Education and elsewhere in his work: problem-or theme-based learning, peer-based learning, learning that is open to the world outside the classroom, and teachers who are engaged as coaches and facilitators rather than authority figures.