Learning environments can support the development of foundational knowledge and promote children's attitudes toward learning and school. This study explores the relation between school enjoyment and general knowledge from preschool (2016–2017) to kindergarten (2017–2018) in 1359 children (Mage = 55, 61 months, female = 50%; 58.5% Hispanic, 17% Black, 10% Asian, 10% White, 5% multiracial/other; linguistically diverse). Cross-lagged panel models showed significant bidirectional associations between preschool enjoyment and change in general knowledge from preschool to kindergarten with a standardized coefficient of β = .21 (p < .001) and associations between preschool general knowledge and change in enjoyment, β = .09 (p = .015). Exploratory analyses with teacher characteristics and demographic subgroup comparisons are discussed. These associations suggest the potential intervention strategy of promoting early school enjoyment to support broader academic development. (author abstract)