Educators have long been rightly concerned about the risk that schools themselves can produce profoundly unsettling and potentially 'unproductive' emotional and physical states among children and youth. This chapter examines two moments in the attentive regimes and engagement paradigms that have been manifest in the material design of schools and classrooms in the United States in the twentieth century. The first part looks at a temporary classroom constructed as part of a demonstration of Montessori pedagogy at the 1915 World's Fair in San Francisco, California. The second section examines the classrooms the Crow Island School built in 1940 in Winnetka, Illinois, a wealthy Chicago suburb renowned for its progressive schools. In both these instances, architects and educators linked design with affect and connected design to strategies for managing boredom. Drawing on scholarship from architectural history and the history of emotions, I treat the ascription of affective effect to school design and architecture as itself a shifting historical artifact worthy of examination. The chapter argues that the confluence of emotional modulation, classroom design, and engagement/boredom management forms an important site in the governing of individuals. [For the complete volume, "Making Education: Material School Design and Educational Governance. Educational Governance Research. Volume 9," see ED614539.]