Many children naturally seek challenging physically active play which may involve injury-risk. Prior studies have attempted to describe the characteristics of risky play but to date none have considered factors that impact on opportunities for risky play or the likely resultant outcomes. Using semi-structured interviews and naturalistic observations, this study aimed to investigate adult attitudes towards risk-taking and whether children's experiences of risky play differ according to the contexts in which the play takes place. Although the children's mothers and Early Childhood practitioners believed risky play was an important aspect of learning and development and encouraged this type of play, observations of children's play at a local playground and their Early Childhood centre revealed that these contexts provided limited opportunities for risky play. Regulatory factors and requirements for playground safety were identified as having a detrimental impact on the quality of play in these settings creating tension between adult beliefs about the benefits of risky play and its provision. (Contains 6 tables.)