Play is essential for learning as it prepares children to understand and approach the challenging realities of life (Bruce, Friedrich Froebel: A critical introduction to key themes and debates. Bloomsbury, 2021). There is an increasing focus on offering outdoor play experiences for infants and toddlers in early childhood education (ECE), however, these experiences can differ widely. A focus on this topic is important as the early childhood curriculum frameworks in both Australia and New Zealand emphasise the importance of young children being active in the outdoors (Australian Government Department of Education [AGDE], Belonging, being and becoming: The early years learning framework (V2.0). Australian Government Department of Education for the Ministerial Council, 2022; Ministry of Education [MOE], Te Whāriki: He whāriki mātauranga mō ngā mokopuna o Aotearoa: Early childhood curriculum, 2017). In this chapter, we draw on video analysis of infant-toddler play in outdoor play environments to highlight the nature and value of embodied risk-taking and to elevate the role of the teacher in ensuring children’s access to play environments that afford opportunities for holistic learning.