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This article highlights possibilities for understanding challenges related to collaborative learning by bringing two complementary lenses into theoretical and empirical conversation—complexity and situativity. After presenting a theoretical comparison that characterizes complementarity between complexity and situativity in order to frame their relative contributions to a systems-level understanding of learning processes, we examine persistently unproductive social activity during a 14-session, collaborative engineering design project in a fifth-grade peer group from both perspectives. We do so in order to demonstrate the value of these complementary perspectives for understanding collaborative learning processes and to suggest different explanations of why unproductive social activity sometimes persists and possibilities for interrupting such dynamics. We thus suggest a shift from explanatory accounts of system processes to prospective processes for systems of action within social ecologies of change. Such a framework can resolve the social activity of collaborative learning around a systems-level orientation.