International evidence indicates there may be little or no academic benefit for children who are retained, and the possibility of negative long term socio-emotional outcomes for these children. Drawing on data from the nationally representative Longitudinal Study of Australian Children (n = 4464), this paper provides an Australian perspective on the practice of grade retention, specifically investigating repeating the Kindergarten year. Our results indicated that nearly half of grade retention occurring by Year 6 occurs in the Kindergarten year, the main reasons being related to learning and behavioural difficulties. The analyses identified a number of child and family factors associated with grade retention, the strongest predictors being maternal mental health and parental receptive language concern, with school readiness, receptive language skills, and child hyperactivity also relevant factors. The paper considers implications for early intervention to support children’s academic trajectories through school.