The chapter takes the discussion into the Contested Region. The chapter opens by exploring what historian Edward Ayers has described as the “culture of dignity.” The culture of dignity, which prevailed across the region, emphasized law, justice, and the intrinsic worth of all human beings as values that constrained the individual assertion of violence. These norms led residents of the region to impose conditions on their toleration of slave catching. The chapter then explores the impact of this culture of conditional toleration on the Underground Railroad. In placing significant limits on the behavior of slave catchers, residents created a safer environment in which fugitives from enslavement could travel more openly and with less assistance. The result was a decline in the intensity of Underground activity as activist networks grew sparser and less organized farther from the Borderland. The particular concern of communities in the region for the preservation of human dignity and due process is further illustrated through an analysis of fugitive slave cases in which cultural missteps by slave catchers alienated communities in the region, sometimes explosively.