Early childhood programs strive to provide good-quality care and education as young children develop their physical, emotional, social, and intellectual skills. In order to provide children with positive, developmentally appropriate learning opportunities, educators ensure the safety and security of children, indoors and outdoors. The outdoor learning environment is an important element of the total care and education of young children. Outdoor spaces can enhance curriculum, especially when teachers responsibly supervise children who are engaged in unstructured play. Supervision is far more than just assuring sufficient teacher/child ratios. This article explores supervision practices that deal with two primary issues: (1) preparation of the outdoor learning environment; and (2) watchful guidance of young children by educators. (Contains 4 online resources.)