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Using qualitative methods, this study describes the transition from Head Start to Kindergarten from the perspective of the family members. Two questions frame the inquiry: (1) What beliefs do family members have about kindergarten readiness? and (2) What experiences of connection do family members describe when their child is enrolled in Head Start, and how do these experiences look when the child transitions into Kindergarten? Preliminary findings show that family members' ideas about kindergarten readiness do not change during the transition. More engagement with the data is needed to understand how family members experience connections with their child's school. This research has the potential to create space for the voices of family members in the literature about family engagement.