ABSTRACTWoody encroachment—the expansion of woody shrubs into grasslands—is a widely documented phenomenon with global significance for the water cycle. However, its effects on watershed hydrology, including streamflow and groundwater recharge, remain poorly understood. A key challenge is the limited understanding of how changes to root abundance, size and distribution across soil depths influence infiltration and preferential flow. We hypothesised that woody shrubs would increase and deepen coarse‐root abundance and effective soil porosity, thus promoting deeper soil water infiltration and increasing soil water flow velocities. To test this hypothesis, we conducted a study at the Konza Prairie Biological Station in Kansas, where roughleaf dogwood (Cornus drummondii) is the predominant woody shrub encroaching into native tallgrass prairie. We quantified the distribution of coarse and fine roots and leveraged soil moisture time series and electrical resistivity imaging to analyse soil water flow beneath shrubs and grasses. We observed a greater fraction of coarse roots beneath shrubs compared to grasses, which was concurrent with greater saturated hydraulic conductivity and effective porosity. Half‐hourly rainfall and soil moisture data show that the average soil water flow through macropores was 135% greater beneath shrubs than grasses at the deepest B horizon, consistent with greater saturated hydraulic conductivity. Soil‐moisture time series and electrical resistivity imaging also indicated that large rainfall events and greater antecedent wetness promoted more flow in the deeper layers beneath shrubs than beneath grasses. These findings suggest that woody encroachment alters soil hydrologic processes with cascading consequences for ecohydrological processes, including increased vertical connectivity and potential groundwater recharge.