Jet impingement quenching as one of the most effective cooling methods is widely applied in many industrial fields. When a subcooled jet strikes the hot surface, the wetting front propagates outside after the wetting delay accompanied by high-frequency fluctuations. To elucidate the propagation behavior of the wetting front and its fluctuation characteristics, the quenching experiments that an upward water jet with different velocities and subcoolings impacted onto a hot nickel block with an initial temperature of 280°C were conducted. The transient transition boiling associated with the intermittent wet and dry situations around the wetting front was quantitatively analyzed based on the visual observation and fast response surface temperature measurement technique. The liquid-solid contact period near the wetting front, under the late transition boiling regime, spans the range of 494–590 µs. This time interval is comparable to the period of disturbance waves induced by the Plateau-Rayleigh instability of the jet. Furthermore, fluctuation amplitude of the wetting front diminishes from 0.8 to 0.2 mm as it propagates. The order of magnitude and the trend of variation in the fluctuation amplitude with respect to the wetting front radius align with theoretical calculations without considering boiling heat transfer effects.