We investigate the phase dynamics of moderately damped NbN/AlN/NbN Josephson junctions and we present experimental results on detailed aspects of phase diffusion processes. We measure both single escape and multiple escape and retrapping events obtaining a crossover temperature T* from Kramers to phase diffusion switching. We observe a clear dependence of the crossover temperature T* by the bias current ramp rate, while the damping factor Q remains the same. The measured effect is in strong agreement with theoretical predictions reported by Fenton and Warburton.