The significance that the book of Ruth plays in the story of the Messiah can be seen clearly at the end of the book, with the genealogy connecting the child given to Naomi through Ruth to David. This is routinely noted by biblical theologians, seen recently in T. D. Alexander (1998), Kaiser (2008), and Schreiner (2013). Their emphasis on this connection is commendable, but they miss an equally vital connection to the messianic storyline at the beginning of the book: the theme of repentance. Some fail to notice this theme altogether (Boda 2015), while others point it out, but fail to identify its significance. It is the goal of this paper to show that a major canonical and messianic theme is being overlooked. I argue that שׁוּב is a keyword in Ruth that contributes to the larger canonical storyline of salvation through Israel’s Messiah. I first discuss the theme of repentance in Ruth before exploring its significance in the canon of scripture. A canonical reading reveals intentional patterns imprinted by the biblical authors between the story of Ruth and the Messianic introduction to Matthew’s Gospel (chapters 1-4). The book of Ruth does not merely identify the lineage of the King but also joins the chorus of scripture in announcing that entrance to the kingdom requires repentance.