Due to the last decades’ discussion on play safety on the one hand, and the benefits of giving children challenges and risks on the other hand, the need has grown for more knowledge on children’s natural risk-taking in play. This article aims to explore how preschool children seek out risk-taking in play and how children and preschool staff manage these risks. In the present study, qualitative video observations of risk play in 29 children were collected in 2 Norwegian preschools. The data in the present study show how children intentionally seek out risk in their play through seeking great heights and high speed and by performing play in hazardous, dangerous and daring manners. Still, the results indicate that children’s risk-taking decisions are balanced between their evaluation of positive and negative outcomes of the play situation. The staff in the present study has quite a liberal attitude towards children’s risk-taking in play and sometimes encourages it. This article contributes a better qualitative understanding of how children engage in risky play.