The purpose of this article is to promote a deeper, more complex understanding of the challenge that "recess time" poses to elementary school educators and to thereby understand the practices in which they are currently engaging. Because teachers are expected to shepherd students through a vast array of learning standards while remaining sensitive to their social, physical, and emotional well-being, decisions about who gets to participate in recess are made under great pressure. Also, teachers often correctly perceive that only limited resources are available to help them. After sharing what the authors have learned about teachers' perspectives, they discuss two examples of school initiatives that support teachers in managing classrooms while ensuring that recess remains part of every child's day. The aim of this article is for educational leaders working on this issue to see the necessity of engaging classroom teachers in the big-picture discussions about recess and related health and wellness policies.