Students with emotional and behavioral disorders often need behavioral supports to facilitate their success in the classroom. One commonly used intervention involves taking brief breaks at targeted times during the day to return to the classroom better prepared for participation. However, research is limited on what should happen while a student is on break. Two potential strategies were evaluated using an alternating treatment design with three students at an urban charter school in 1st and 5th grades. Following a baseline phase, breaks alternated between a mindfulness-based intervention (MBI) involving awareness of breath, body, and self and a relationship-based intervention (RBI) involving a "would you rather" get-to-know-you game. Results suggest both interventions improved behavioral outcomes for all participants compared to baseline. For two students, no clear break type had a more profound impact. For one participant, data suggest that MBI was a superior intervention for increasing academic engagement. Both interventions were implemented with acceptable fidelity and social validity. Limitations and future directions are discussed.