and ground-state entanglement in the ultrastrong-coupling (USC) regime, where coupling strengths are comparable to subsystem energies. Despite progress in many experimental platforms, the few experiments reaching USC have been limited to spectroscopy: demonstrating USC dynamics remains an outstanding challenge. Here, we employ a circuit QED chip with moderate coupling between a resonator and transmon qubit to realise accurate digital quantum simulation of USC dynamics. We advance the state of the art in solid-state digital quantum simulation by using up to 90 second-order Trotter steps and probing both subsystems in a combined Hilbert space dimension ∼80, demonstrating the Schr\“odinger-cat like entanglement and build-up of large photon numbers characteristic of deep USC. This work opens the door to exploring extreme USC regimes, quantum phase transitions and many-body effects in the Dicke model.