The Jews of medieval Ashkenaz are often perceived as more insular than their co-religionists to the south and the east, as reluctant participants at best in the cultural trends of their day. Yet read in conjunction with local archival and legal materials, discussions in the rabbinic responsa from German-speaking lands demonstrate that both rabbis and laypeople were well-versed and willing participants in many of the same legal and economic institutions as their Christian neighbors. My paper will focus on several medieval German methods of guaranteeing loans that are referenced and debated in the rabbinic responsa of the late thirteenth and early fourteenth centuries. Close analysis of these economic instruments and their treatment in rabbinic discourse will highlight the ways in which Ashkenazi Jews of all stripes adopted and adapted elements of their local legal environment. I will show that rabbinic texts sometimes provide details and insights into common practices that are not documented elsewhere; and I will argue that they offer a unique perspective onto Jewish participation in and contributions to medieval legal culture at large.