The intertextual connections that the book of Ruth makes to the book of Proverbs, and especially to the Valiant Woman of Prov 31, suggests that the author intended the narrative to be read in a particular way. The canonical context of the book of Ruth, when situated with wisdom literature in the Writings, is a recognition of this, as is the modern reception of Ruth as an exegesis or actualization of the Valiant Woman character. But in this essay, I argue that this latter reading strategy fails to capture exactly how Ruth relates to the book of Proverbs and to the wisdom genre in general. In contrast to commentators who have interpreted the book as a demonstration of wisdom values within a narrative setting, I suggest that the book of Ruth can be understood as an extended problematization of the limits of wisdom expressed in categorizing discourse. Ruth attempts a destabilization of some of the authoritative claims made about conventional wisdom as expressed in the book of Proverbs. Categories of conventional wisdom are set up, only to be destabilized and complicated throughout the text. This reading of the book of Ruth brings it much closer to the other two texts that make up Israelite wisdom literature: the books of Job and Qoheleth, which also reflect on and complicate conventional wisdom. Ruth can therefore be understood in relation to the wisdom genre—but the relationship is more complex and nuanced than commentators have hitherto realized.