Previous research has highlighted the effectiveness of supporting parents in fostering children’s academic and/or social-emotional development in preparation for kindergarten. Considering the emergence of COVID-19 as a risk factor to which all children and parents have been exposed, it is essential to understand parental mental health as it relates to early childhood development. This study utilized mixed methods to examine the experiences and perspectives of parents (N = 82) whose children were transitioning into kindergarten during the fall of 2020 amidst the COVID-19 pandemic. Results indicate that parents’ knowledge/confidence in managing their child’s transition to kindergarten was inversely associated with their worry during this time and may be a meaningful target for future interventions. Implications regarding how to best support and include parents in early intervention programming prior to kindergarten entry are discussed