Cross-case study research was used to explore the school readiness of four 5-year-old children entering kindergarten during the 2020–2021 school year after three or more years of play-based early childhood education at a Reggio Emilia-inspired early childhood education center. Data included a series of three 1-h individual interviews with four mothers and three kindergarten teachers, field visits during remote learning, and artifact collection over the course of the school year. Themes describing the children’s school readiness were developed through cross-case analysis. Participants described the children as learners, explorers, communicators, and empathizers. The learner theme centers on the children’s responsiveness to instruction; the explorer theme describes how the children approached learning; the communicator theme illustrates the children’s prowess with social connection and self-advocacy, and the empathizer theme shows the thoughtfulness and emotional sensitivity these children displayed. (author abstract)