High speed rail demands precision structural health monitoring in shallow underground environments near embankments. Traditional low frequency wireless channels can communicate with underground sensors, but its large antenna elements are prone to damage from geological stress. In this case study paper, we design a higher frequency compact system and experimentally characterize its performance in-situ, in different soil and moisture conditions that are representative of UK soil conditions near the planned HS2 rail site and weather conditions. Accurate 3D electromagnetic simulation results are also shown to support experimental results and a pathloss model sensitive to soil conditions is developed to inform upcoming high speed rail embankment monitoring deployment. The multi-disciplinary findings presented will also directly inform the depth and data reliability of current high speed rail sensor deployment.