The purposes of this research were to explore the effectiveness of the Chickasaw Nation early care and education program in promoting school readiness while infusing tribally relevant values in children from birth through age five; engaging parents in all aspects of their children’s learning; and supporting children and families through the transitioning to kindergarten. The study used qualitative methods to examine the experiences and perceptions of ten parents, ten teachers, and five administrators within Chickasaw Nation’s early care and education system regarding the four basic areas of school readiness, parent engagement, transition, and culturally relevant pedagogy. Four primary themes emerged from the semi-structured interviews: 1) socialization, school readiness, and transition, 2) learning, curriculum, and assessment, 3) the role of parents, and 4) cultural integrity. Data were collected through semi-structured interviews, transcribed, and analyzed based on four research questions. Findings indicated parents, teachers, and administrators were satisfied that the program was successful with assisting children in making progress toward achieving developmental and school readiness goals and that the children were physically, socially, emotionally, and cognitively prepared to enter kindergarten. The program provided activities to encourage and promote parental involvement; however, parents did not indicate active involvement or participation in the activities. There was little evidence to support culturally relevant pedagogy alignment with curriculum and practices. Implications for additional research focusing on American Indian children in preschool programs and the importance of instilling pride and culture are recommended.