Critical slowing down of the time it takes a system to reach equilibrium is a key signature of bistability in dissipative first-order phase transitions. Understanding and characterizing this process can shed light on the underlying many-body dynamics that occur close to such a transition. Here, we explore the rich quantum activation dynamics and the appearance of critical slowing down in an engineered superconducting quantum circuit. Specifically, we investigate the intermediate bistable regime of the generalized Jaynes-Cummings Hamiltonian (GJC), realized by a circuit quantum electrodynamics (cQED) system consisting of a transmon qubit coupled to a microwave cavity. We find a previously unidentified regime of quantum activation in which the critical slowing down reaches saturation and, by comparing our experimental results with a range of models, we shed light on the fundamental role played by the qubit in this regime.