The sixteenth-century Sephardi communities of the Ottoman Empire were hothouses of exegetical creativity. New commentaries and collections of homilies written in Safed and Salonica testify to the widespread, rigorous, and innovative biblical scholarship that flourished among post-Expulsion scholars. As Joseph Hacker has shown, many of these expositions had their origins in sermons and homilies, and were thus informed by the interests and experiences of communal rabbis and their communities. The purpose of this paper is to examine the commentaries of Moses Almosnino, Moses Alsheikh, Solomon Alkabets and Samuel de Uceda on the book of Ruth. The exegetes express a common concern regarding the mobility of Ruth and Naomi, asking why the women undertook the journey from Moab to Bethlehem alone, how they found their way without a male guide, how they protected themselves from attack, and whether Ruth acted modestly in travelling to Boaz’s field in a group. This paper will ask why and how these authors considered these questions by examining contemporary expressions of concern regarding women’s mobility, including the responsa of Samuel de Medina and the 1564 letter of Abraham Palieche. By thus investigating how these commentators’ expectations regarding women’s mobility shaped their interpretation of the book of Ruth, this paper will contribute to a fuller understanding of how early-modern Sephardi communal rabbis interwove their own insights and concerns with earlier interpretations of the Hebrew Bible in order to compose original exegetical discourses.