Much as the long-accepted view that Rashi was intellectually isolated from his Latin milieu in northern France has been challenged in the last two decades of the twentieth century, recent scholarship calls for reconsideration of the earlier tendency to minimize the cultural ties between the Ashkenazic community and Jews in Muslim lands during the eleventh century. Increasing evidence points to continuous trade among Jewish centers in Christian and Muslim lands, especially between the Rhineland, where Rashi studied, and Byzantium, al-Andalus, North Africa, and Iraq. It probably was along one of these routes that the Babylonian Talmud and the teachings of the Geonim first came to the Rhineland. Based on indications that Rashi had access to Jewish learning in Muslim lands, Avraham Grossman has argued that a key impetus for Rashi’s peshat revolution was his awareness of the Judeo-Arabic peshat tradition that had reached maturity in al-Andalus by the eleventh century. The current chapter aims to evaluate that theory.