Despite its rapid growth in the last few decades, organizational paradox research remains limited in understanding the (dis)equilibrating dynamics of the paradoxes involved in organizing risk. The need is especially acute in the context of complex interorganizational systems where risk is a paramount concern and multiple organizational paradoxes coexist. To address this need, this study charts the adaptive journey of a regulatory organization when navigating the (dis)equilibrating dynamics of multiple paradoxes in an interorganizational system. The process model that emerges from our study highlights phronetic pivoting, first, as change-ups in the regulatory space that shift the power dynamics with oscillation toward equilibrium in seemingly disequilibrating ways and, second, facilitates the learning of oscillation grounded in the power/knowledge practices of competing regulatory philosophies. We discuss the significant implications of our findings for the theory development of organizational paradox and organizing risk.