In the city setting in which this article's investigation took place, high school dropout rates have remained above 50% for better than three decades. This article reports on a photographic inquiry into urban youth's perceptions of the very institution of school, revealing reasons behind the multigenerational school disengagement represented by these graduation rate statistics. relying on visually based mechanisms with which city students are already proficient, the findings suggest that these tools can provide previously inaccessible data on school detachment as well as deepen our perspectives on what these youth believe about school leaders and leadership. (Contains 9 figures.)