Homiletical Theology understands the work of preaching to be continuing the “unfinished” task of theology. Embracing a fundamentally provisional nature, homiletical theology understands its work as the continual negotiation of the message of the Gospel with the contexts into which preaching speaks. This unfinished quality raises questions for how the preacher, in their theological task, navigates the various theological traditions they encounter. Using the example of the “sour grapes” proverb found in both Jeremiah and Ezekiel, this article explores how Scripture itself wrestles with theological traditions to consider how present-day homiletical theologians might continue to wrestle with their “unfinished” task.