This study presents a method for identifying strategic locations to drill additional boreholes by quantifying and reducing subsurface uncertainties in geotechnical site investigations. The case study is the Red Roof landslide site located near milepost 140 on US Highway 26/89 in Teton County, Wyoming. A landslide remediation report had recommended additional boreholes before completion of the project. Two primary sources of uncertainty in geomaterials, namely geological and ground, are evaluated to determine the locations for these additional boreholes. The study aims to enhance site characterization and improve the accuracy of geotechnical assessments by strategically selecting and drilling additional boreholes that will reduce these subsurface uncertainties. The method involves reviewing and collecting the available site investigation data. An extensive geostatistical simulation is conducted based on the available data to identify spatial locations at the site that have uncertain subsurface conditions. Data from the additional boreholes could be utilized in these areas to reduce the uncertainty. This approach aligns with the current multi-phasing of site investigation in engineering practice, where a preliminary investigation is conducted before a detailed investigation. The results show that the locations of additional boreholes identified using this method differ from the ones earlier recommended, showcasing the effectiveness of the methodology in this application. This study also provides insights into effective strategies for reducing uncertainties through strategic borehole placement in similar geotechnical investigations. By quantifying geological and ground uncertainties, the method enables informed decision-making for slope stability analysis and risk assessment, with implications for infrastructure stability and geohazard mitigation.