Background: School recess offers students a break from the rigors and immobility of academic learning, and a chance for social interaction, play, and physical activity. The recess literature is based on elementary schools, with little attention to older students. Early adolescents also need school breaks, and this study offers some of the first findings on how to organize this time to best support the developmental needs of middle schoolers. Methods: The study explores middle school breatktime in 3 schools in California. It uses observations, interviews, and a student survey conducted in 2018. Data were coded thematically and analyzed. Results: Findings indicate a tradeoff between socialization and physical activity among students who falls along age and gender lines. Adults viewed their roles mainly as safety monitors, including both physical and emotional safety. They were aware of the limitations of their breaktime offerings, which generally included access to outdoor and a few alternative indoor spaces, and attributed not having more options to lack of resources. Conclusions: Findings demonstrate the complexities of organizing breaktime space for early adolescents. Middle schools must plan their breaks with attention to developmentally appropriate activities, including games and sports as well as opportunities for other kinds of social interactions in safe, supportive environments.