AbstractUnsaturated soil contains pore air, some of which becomes entrapped in the soil layer during the infiltration process. Such entrapped pore air in the soil layer inhibits infiltration, decreases hydraulic conductivity, and causes erroneous estimates of groundwater response. Experimental studies suggest an effect of compressed entrapped pore air on stream discharge. However, few studies have investigated the behaviour of pore air in the field, and no method for measurement of pore‐air behaviour has been established. We measured pore‐air pressure (Pair) with a simple handmade probe, combined with atmospheric pressure (Patm) and groundwater level. The entrapment and compression of pore air were detected based on the pressure difference (ΔP = Pair – Patm). Observations were conducted for approximately 1 year in two small headwater catchments (TC and HA, which have differences in soil depth and groundwater level dynamics) in Ibaraki Prefecture, Japan. Positive responses of ΔP during some rainfall events were confirmed at both TC and HA. Pore‐air entrapment occurred even during weak rainfall events with rainfall intensity of <10 mm/h. During a typhoon event in October 2019, a maximum ΔP of 3.9 kPa was observed at HA. The pore pressure increase recorded by the tensiometer was mostly explained by the increase in ΔP, which was supported by the soil moisture data. Therefore, we concluded that our handmade measurement system could successfully measure Pair and detect pore‐air entrapment in the field. This showed that Pair is not negligible. Total event rainfall was related to the maximum ΔP. It also showed that the rise in the groundwater level plays a significant role in pressurization of the entrapped pore air. We present the first field data demonstrating the effect of groundwater level rise on the pressurization of entrapped Pair.