The transition to kindergarten is a critical milestone in children's lives, with implications for academic and future life success. The demographic family/parental variables of residence, social class, and race have been associated with children's adjustment to kindergarten. In particular, children growing up in families from urban, low-income African American backgrounds are at heightened risk for negative academic, cognitive, and socio-emotional outcomes as they transition to kindergarten. Relatively little inductive research exists on the kindergarten transition of this population and how families from urban, low-income African backgrounds positively support their children's kindergarten adjustment. However, researchers using qualitative methods are increasingly examining the first-hand experiences of families from urban, low-income African American backgrounds to better understand family beliefs and practices that promote children's successful kindergarten transition. Contributing to this gap in the literature, we utilized qualitative interviews informed by resilience theory to explore how 20 mothers from urban, low-income African American backgrounds facilitated their Head Start preschoolers' transition to kindergarten. We found that, despite possessing parental/family risk factors associated with ineffective kindergarten transitions, mothers monitored and assessed their children's academic and socio-emotional school readiness abilities, promoting readiness competencies while addressing readiness weaknesses. One of the ways that mothers supported children's transition readiness was through one-on-one conversations with preschoolers. Our findings provide recommendations for effective home-school collaborations that support children's successful kindergarten transition. Collaborating with engaged and motivated parents, Head Start can assist families and children prior to kindergarten and continue to serve as a link between families and children and elementary schools.