The transition to kindergarten is regarded as a critical time for both children and families, especially for families with low incomes who are at greatest risk for educational challenges. Most studies focus on the school perspective as children enter classrooms, and less scholarship focuses on the family perspective. This paper shifts the conversation to the context of the family and how families understand and experience kindergarten entry. As part of a larger qualitative study on the transition to school, 24 parents participated in semi-structured interviews where they described the process of preparing children for kindergarten before school entry, and then reflected on the actual process 1 year later. Based on a thematic analysis of interview data, four main themes emerged: (1) The transition is still going, (2) Logistics were the toughest part, (3) I told you this would happen, and (4) The first time is the hardest. Findings from this study generate new knowledge related to the lived experiences of families from lower-income backgrounds, as well as many of the challenges they encounter with the educational system. Supporting the transition to school requires the building of relationships with families and examining the family context in addition to the school context. Implications for early childhood personnel and schools are discussed.