Many school districts provide one-time transition events to help students prepare for the rigors of kindergarten; yet, research shows families desire additional information and opportunities to help their children thrive once school begins. Researchers for this study interviewed 39 parents whose children participated in a three-week structured kindergarten transition program designed to promote parental involvement in school, reduce students’ chronic absenteeism, and increase children’s readiness for kindergarten. All interviewees expressed that participating in the program yielded benefits for themselves and their children. Respondents shared that meeting education staff members early during the summer, familiarizing themselves with the layout and routines of their schools, and building stronger social connections with other families were of particular value in helping them prepare for the start of kindergarten. Similarly, understanding kindergarten expectations more thoroughly and acquiring tools to support their children at home were deemed especially beneficial for those families who had not previously participated in preschool or other structured school opportunities. In addition to positive feedback, participants proposed various ways that adjusting the program could better meet the needs of all stakeholders. Suggestions included increasing the length of the student sessions, improving communication between district and families, re-structuring the parent information sessions to be more conducive to working families, and staffing the program with more individuals who would stay on as teachers during the transition from summer to fall. Parent suggestions from this study were synthesized into multiple implications for practice and substantiated by current relevant literature.