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This essay argues that Augustine structures his famous analysis, in Confessions 2, of his theft of pears by his understanding of the mode of insight rather than by his understanding of the mode of discovery. Therefore, while Augustine’s study explicitly includes what he thinks are the stages by which his audience can discover his principal insight that human nature is imago Dei, i.e. spiritually united with a Self-Sufficient and Creator God for the sake of attaining perfect union with Him, it is entirely from this imago Dei perspective that Augustine presents his account of the pear theft. Recognizing the center of Augustine’s approach, moreover, offers his reader two closely related benefits. These are opportunities, first, to overcome various limited criticisms and interpretations of Augustine’s analysis of the pear theft and, second, to see how Augustine’s rhetorical manner of confessio represents his perspective of insight.