This monograph investigates, from a distinctive philosophical perspective informed by pragmatism, the relation between the transcendental and the transcendent. It not only develops a viable form of pragmatic transcendental naturalism (which the author has defended in earlier works) but examines the intertwining themes of sanity and illusion, arising through critical considerations of approaches to transcendence that fail to take seriously human finitude. Issues discussed range from those found in metaphysics and epistemology to those in ethics and philosophy of religion. They are all intimately related to each other by offering variations of aspirations to reach toward transcendence – and, in many cases, of the illusoriness of those aspirations. This illusoriness is something that requires thoroughgoing pragmatic and transcendental critique, combining argumentation strategies drawn from philosophers as different as Kant, Wittgenstein, and William James. This critique leads, among other things, to a radical rearticulation of how philosophy of religion as a sub-discipline of philosophy ought to be practiced. This text appeals to researchers and graduate students working in these fields.