Vadose zone characterization and monitoring immediately below landfills using horizontal boreholes is an emerging technology. However, this topic has received little attention in the peer-reviewed literature. The value of this approach is that activities are conducted below the waste, providing clear and rapid verification of containment. Here we report on two studies that examined the utility of horizontal boreholes for environmental characterization and monitoring under radioactive waste disposal pits. Both studies used core sample analyses to determine the presence of various radionuclides, organic compounds, or metals. At one borehole site, water content and pore-water chloride concentrations were also used to interpret vadose zone behavior. At another site, we examined the feasibility of using flexible membrane liners in uncased boreholes for periodic monitoring. For this demonstration, these retrievable liners were air-injected into boreholes on multiple occasions carrying different instrument packages for environmental surveillance. These included a neutron logging device to measure volumetric water at regular intervals, high-absorbency collectors that wicked available water from borehole walls, or vent tubes that were used to measure air permeability and collect air samples. The flexible and retrievable liner system was an effective way to monitor water content and measure in situ air permeability. The high-absorbency collectors were efficient at extracting liquid water for contaminant analyses even at volumetric water contents below 10%, and revealed tritium migration below one disposal pit. Both demonstration studies proved that effective characterization and periodic monitoring in horizontal boreholes is both feasible and adaptable to many waste disposal problems and locations.