My project seeks to chart out an account of Dewey’s philosophy of education, relating to its practical application in the work of Lipman. I then present various current trends in the way that learning environments have changed both over the past few decades with reference to technological development, and in the last year with reference to the coronavirus pandemic. Ultimately, I argue that the main thing preventing a realization of Dewey’s democratic ideal is ‘datafication’, the phenomenon of reducing educational efficacy to quantifiable metrics and abstract information. Due to the insistence of Dewey and Lipman on education as a facilitation of meaningful experience, I hold, datafication makes the manifestation of any true practice of Deweyan pedagogy impossible.