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Dynamically transitioning between individual and collaborative learning has been hypothesized to have positive effects, such as providing the optimal learning mode based on their needs at the moment. There are, however, challenges in orchestrating these transitions in real-time while managing a classroom of students. AI-based orchestration tools have the potential to alleviate some of the orchestration load for teachers. In this study, we describe co-design sessions with teachers where we refine prototypes of an orchestration tool to support dynamic transitions based on findings from previous user research. Our findings resulted in prototypes of the technology and insights from teachers regarding pairing strategies, data needed while pairing, and the AI’s role.