Downward mobility is common, but we know little about who falls from the upper-middle class, how, and why they don’t see it coming. This chapter provides an overview of how intergenerational downward mobility occurs. It shows that both resources and identities are associated with downward mobility from the upper-middle class. Individuals who inherit relatively high levels of academic knowledge, institutional insights, and money tend to develop an identity that leads them to maintain high levels of these resources. They use these resources to reproduce their class position. Individuals who inherit relatively low levels of academic knowledge, institutional insights, or money tend to develop an identity that encourages them to maintain their resource weaknesses. Without the resources that schools, colleges, and professional workplaces reward, they tend to enter downwardly mobile trajectories. They do not necessarily anticipate their impending downward mobility as they observe times when they or their parents moved toward class reproduction while not having high levels of these resources.