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Parents, being the first teachers for their children, develop and acquire expectations essential to developmental domains, and education. A transcendental phenomenological study explored Caribbean immigrant parents’ cultural perspectives on preparing their children for kindergarten. Data analysis used the four steps of the philosophical phenomenological method: (a) epoche, (b) phenomenology reduction, (c) imaginative variation, and (d) synthesis. Four major themes emerged from the participants’ representation of their cultural perspectives: (a) balancing expectations, (b) developing relationships, (c) investing in your child’s education, and (d) creating lifelong critical thinkers. These findings demonstrate that parents’ cultural differences, values, and perspectives play a crucial role in preparing, developing, and promoting children’s early learning.