As technology enables us to communicate with one another in unpredictable ways that allow for an unprecedented public exchange of diverse ideas, cultivating the philosophical habits of an engaged fallibilistic pluralism gains in urgency. The emergence of the World Wide calls us to consider how an ethics of philosophy might enable us to cultivate practices of communication capable of creating enriching communities in a digital age. In Pragmatism and the Cultivation of Digital Democracies, I draw on Richard Bernstein’s account of the ethos of pragmatism in his 1988 Presidential Address to the American Philosophical Association and on the thinking of Charles Peirce and John Dewey to advocate for practices of digital communicative transaction rooted in the habits of an “engaged fallibilistic pluralism.”