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This contribution traces the dialogical strategies deployed by Augustine of Hippo (354–430) in the Sermons as a case-study on intra-religious encounters in 4th century North-Africa. Specifically, this contribution carries out a chronological-thematic analysis of Augustine’s rhetoric of the image with special attention to the effects that the preacher/hearer dialectic produces in the social ‘moral imagination’. It is argued that ambiguity best characterizes the dialogical strategy inherent to Augustine’s preaching on the interplay between grace and free will. The effect of ambiguity is not persuasion but rather the shaping of a ‘moral imagination’ of a community and thus conditions the sphere of moral action. To conclude, dialogical ambiguity in Augustine’s Sermons simultaneously empowers and constrains the boundaries for the possibility of moral action where free will and grace constantly overlap.