This dissertation investigates changes in the practice and perception of begging in the fourteenth and early fifteenth centuries in southern German towns. It was in this period that German cities began to pass some of the first begging legislation in Europe and to categorize types of "false" beggars. Examining these legislative innovations within their local and charitable context, this dissertation makes two arguments about the place of begging in medieval society. First, the early begging laws were one element of a complex network of begging and almsgiving. Donors, lawmakers, writers, and artists experimented with new approaches to the begging poor in the late Middle Ages, expressing attitudes that were often contradictory and which fluctuated over time. Yet a general acceptance of begging as a method of survival for the poor remained normative, and medieval people often desired to have a population of beggars easily available to serve as recipients of almsgiving. Second, the continued centrality of begging shaped how the poor themselves understood their place in society, exposing them to traditional Christian ideas about almsgiving which they could have internalized and adapted. This dissertation has two parts. The first half contains case studies of Nuremberg, Augsburg, and Constance, the first three German cities to regulate begging and to categorize types of beggars. These studies nuance the negative view of beggars suggested by an isolated reading of the first begging laws, revealing instead a complicated interplay between local events, rising suspicions of begging, and continued impulses toward charity. The second part expands these three case studies with evidence from surrounding German cities to examine thematic topics. As most of the early German begging legislation sought to regulate which people could beg and where they could do so, this section examines how perceptions of beggars were reflected spatially in attempts to regulate permissible begging locations, and then considers how and why medieval donors discriminated among the poor. The final chapter then reverses these donor-centered approaches to charity and considers almsgiving from the perspective of a beggar, as the begging poor were also active participants in medieval charitable exchanges.