The Gudaga Goes to School study described the early school experiences and transition to school for a birth cohort of urban Aboriginal children living in Sydney, Australia. A life course approach identified the complex range of factors involved in transition to school for this cohort and their families. This chapter presents parent perspectives, supplemented with information from children’s teachers, to show the range of experiences of parent involvement at school. Three case studies have been developed, drawing on a series of interviews conducted between 2011 and 2015, prior to the child starting school and up to the end of Year 2. Parents reported positive school experiences and support of their child’s successful transition to school. They placed importance on relationships, communication, a welcoming environment and school support of children’s learning and school engagement. Challenges and barriers to involvement, if and how these were overcome, and areas for improvement are discussed.