We show the transition from a fully quantized interaction to a semiclassical one in entangled small-number quantum systems using the quantum trajectories approach. In particular, we simulate the microwave Ramsey zones used in Rydberg-atom interferometry, filling in the gap between the strongly entangling Jaynes-Cummings evolution and the semiclassical rotation of the atomic internal states. We also correlate the information flowing with leaking photons to the entanglement generation between cavity field and flying atom and detail the roles played by the strong dissipation and the external driving force in preserving atomic coherence through the interaction.