While research has investigated risk-taking in play for children from the age of four years upwards, less is known of risky play with children under four years. A small-scale observational study with children from five childcare settings with differing characteristics was undertaken to explore the occurrence and characteristics of risky play for children under four years of age, in relation to the current understanding of risky play. The study found similarities across the different contexts, which seem to reflect the characteristics of risky play for children aged one to three years. The findings suggest that the existing definition and characteristics of risky play are appropriate for two- and three-year-old children, but for one-year-olds, the study found discrepancies indicating deviations from existing definitions, indicating that the concept may not be so useful for this age group. To develop understanding of risky play, this article suggests new categories and an adapted definition.