Though Beverly Cleary was a prolific author of children’s literature over the second half of the twentieth century, her fiction has largely escaped critical attention. This article examines the author’s representation of economic insecurity across her Ramona series, arguing that the economy functions as a dynamic setting that mirrors changes in the US economy throughout the fifty years the series was written. Reading the novels through a social-historical lens illuminates the ways in which Cleary’s novels are simultaneously timeless and firmly rooted in their social contexts. Influenced by her own childhood experiences of economic insecurity, Cleary explores the emotional effect family financial struggles have on children within the context of otherwise "light" fiction. Attending to Cleary’s treatment of the economy in her novels reveals the ways in which the author used her fiction to take on the work of authorial alloparenting, normalizing the experience of economic insecurity within families, and modeling personal resilience in the face of difficult circumstances.