Measurements of vadose zone water pressure using custom-made tensiometers provided insight into the dynamics of rainfall-induced infiltration events in a 22-m-thick sandy formation. The tensiometers, based on vadose zone sampling ports, were assembled in a vadose zone monitoring system that allowed in situ, real-time measurements of the temporal variation in vadose zone water content and pore water pressure. Results revealed the critical relationship between temporal variations in vadose zone water content and water pressure, as well as the dynamic connectivity of the vadose zone gas phase to the atmosphere. As expected, variation in the sediment water contents, induced by infiltration events across the vadose zone, resulted in corresponding variations in pore water pressure; however, the measured responses of sediment water pressure to wetting events were delayed compared with the measured variations in water content. The delay in the pressure response to a wetting process varied with location as well as between wetting events. Most of the time, the vadose zone gas phase was well connected to the atmosphere; however, this connectivity was limited during rain events and, therefore, compensation of the measured water pressure variation for the measured atmospheric pressure fluctuation is not straightforward. Connectivity of the vadose zone gas phase to the atmosphere was reestablished simultaneously across the entire vadose zone following redistribution of the percolating water in the upper part of the cross-section.