This essay considers U.S. civics education policy in Puerto Rico from 1900 to 1904. Civics education in Puerto Rico during these years offers a particularly unique context for exploring education at the edge of empire during the dawn of the twentieth century. The article begins with a discussion of civics education in the United States around that time, followed by an explanation of why Puerto Rico offers such a unique context for its consideration. It then examines civics education policy in Puerto Rico during the administrations of Education Commissioners Martin Brumbaugh and Samuel Lindsay within the context of contemporary civics education discourse.