In 2017, 5019 educators from primary and preschool settings across Victoria, Australia took part in joint professional learning around effective transition to school processes. Upon registering for this professional learning workshop, participants were invited to identify the most significant challenges associated with transition to school. The responses were analysed using qualitative content analysis to code emerging themes. Findings show that prior to attending the professional learning workshop, school readiness was identified as a challenge, however perceptions as to what this entailed varied. In many instances the early childhood educators' perceptions of school readiness differed to the views of primary school educators. Whilst academic readiness was identified as an important challenge in both sectors, early childhood educators also raised social and emotional readiness as a key challenge, more so than primary school educators. Educators' awareness of differences in perspectives between early childhood educators, school educators, and parents were also factors noted as key challenges impacting transition to school.