Whilst there appears to be agreement between Jewish and Christian scholars that the author of Ruth was the prophet Samuel, the placement of Ruth (one of the five Hebrew Megillot or scrolls) is to be found in the third division, or the Writings (Ketuvim), of the Hebrew Bible. It was written in Hebrew sometime between the 6th and 4th centuries B.C.E. In most Christian canons it is treated as one of the historical books and placed between Judges and 1 Samuel.
The book does not name its author. It is traditionally ascribed to the prophet Samuel (11th century BCE), but Ruth's identity as a non-Israelite and the stress on the need for an inclusive attitude towards foreigners suggests an origin in the fifth century BCE, when intermarriage had become controversial (as seen in Ezra 9:1 and Nehemiah 13:1). A substantial number of scholars therefore date it to the Persian period (6th–4th centuries BCE). The genealogy that concludes the book is believed to be a post-exilic Priestly addition, as it adds nothing to the plot; nevertheless, it is carefully crafted and integrates the book into the history of Israel running from Genesis to Kings. https://en.wikipedia.org/wiki/Book_of_Ruth
The Sections and Books of the Tanakh (Judaism):
The Torah or Instruction (in its original sense): Genesis, Exodus, Leviticus, Numbers, Deuteronomy.
The Neviʾim or Prophets: Joshua, Judges, Samuel, Kings, Isaiah, Jeremiah, Ezekiel, the Book of the Twelve Prophets.
The Ketuvim or Writings:
Poetic: Psalms, Proverbs, Job
Megillot (scrolls): Song of Songs, Ruth, Lamentations, Ecclesiastes, Esther
Historical: Daniel, Ezra, Nehemiah, Chronicles
Compare this with the order of the books in the Old Testament (Protestant Christianity):
Pentateuch: Genesis, Exodus, Leviticus, Numbers, Deuteronomy
Historical: Joshua, Judges, Ruth, 1–2 Samuel, 1–2 Kings, 1–2 Chronicles, Ezra, Nehemiah, Esther
Wisdom/Poetic: Job, Psalms, Proverbs, Ecclesiastes, Song of Songs
Prophetic: Isaiah, Jeremiah, Lamentations, Ezekiel, Daniel, 12 Minor Prophets
From this, it seems that the Hebrew Tanakh of Judaism has never placed the book of Ruth after Judges and before Samuel. Rather, the book of Ruth appears in the section that contains Song of Songs, Lamentations, Ecclesiastes and Esther. This would be the arrangement familiar to Jesus.