The future state of the redeemed human being in heaven is difficult, if not impossible, to pin down in this life. Nevertheless, Augustine and Anselm speculate on the heavenly life of the human being, proceeding from certain theological premises gathered from Scripture, and their arguments often both mirror and complement one another. Because Anselm and Augustine hold the premise that human beings in heaven are “equal to the angels” (Luke 20:36), our understanding of the heavenly condition of the human can be illuminated by angelology, and vice-versa; each reveals the nature of the other. The paper examines aspects of the positions of Augustine and Anselm on the original state of the angels, their fall, and their confirmation, and then explores the condition of prelapsarian Adam and the transformation of the elect in order to illuminate how these figures conceive the afterlife. The angelologies (and demonologies) of Augustine and Anselm help one to understand the heavenly goal of human life, how the redeemed state of human beings differs from their original condition in Eden, and why there is no redemption for the fallen angels.