This essay explores with the help of the discipline of philosophy of education the educational implications of the practice of canceling individuals or ideas. In particular, it investigates what gets lost or undermined when we cancel various opinions, words, and practices. To advance my argument, I first introduce some basic definitions while analyzing the problem with the notion of cancel culture. Then, I briefly review various historical examples of canceling going back to Socrates. The next part of this paper presents some of the philosophical arguments against canceling and restricting speech made by John Stuart Mill. After presenting Mill's contentions in favor of liberty of expression, I revisit John Dewey's conception of democratic association in order to show that the practice of canceling people and ideas is antithetical to Dewey's dynamic view of democracy. Based on the insights of Mill and Dewey, in the final part I attempt to make an educational case against the practice of canceling.