Understanding is a concept largely absent from contemporary epistemology in which propositional knowledge reigns supreme. I argue that we should move understanding to center stage. I identify three different paths to understanding. I begin with some recent analytic discussions of the value of knowledge and our epistemic goals to show how understanding has crept up there. I then move to recent debates concerning know-how. Surprisingly, one finds an appeal to understanding in certain versions on both sides of the know-how debate, i.e. in both intellectualists and anti-intellectualists. I’m particularly interested in what’s been called “radical anti-intellectualism” (Stephen Hetherington) where understanding is put forth not in name, but in substance. I push Hetherington’s position on know-how in a certain direction that takes it close to a Heideggerian conception of understanding – a conception which is more deeply practical than the others. I’ll indicate at the end some implications of deep practicalism for epistemology.