The Whitby Mudstone Formation has one of the highest landslide densities in the UK with 42 landslides per 100 km2. Landsliding at Hollin Hill in North Yorkshire, UK is complex and continuing, and includes shallow, retrogressive rotational failure on the upper slope, translation, and flow from the base of the Whitby Mudstone Formation over the scarp slope of the Staithes Sandstone Formation. Surface observations augmented by information relating to lithological, moisture and strength variation with depth allowed rapid initial interpretation of the masses affected by movement. These were provided by a single person operating portable probes providing depth logs of cone penetration resistance and soil moisture based upon dielectric property measurements in conjunction with a sampling auger. The gathered information was used to guide the design of further invasive site investigation and the configuration of permanent systems to monitor changes in dynamic moisture distribution and direct movement. At Hollin Hill, the near-surface materials in the upper 5 m interval are distinctly weathered or destructured, predominantly comprising silty clay in the Whitby Mudstone Formation, and fine silty, clayey sand and silty clay in the Staithes Sandstone Formation. Direct and secondary evidence was observed showing high moisture variation to be related to narrow intervals within the upper 5 m. Cyclic variation in moisture has played a key role in the movement and break-up of sliding materials, especially within the prograding lobes resulting from flow over the Staithes Sandstone Formation. Since these observations, permanent monitoring systems have been installed, including electrical resistivity tomography (ERT) arrays, which have successfully mapped the distribution of the Whitby Mudstone and the Staithes Sandstone, but will also be used in time lapse mode to image the near-surface moisture movement driving the landsliding processes. ERT array installations included a large area, low spatial resolution grid designed to investigate the potential coupling between the upper and lower slope hydrogeological processes and a small area, high spatial resolution grid designed to investigate the hydrogeological processes driving the earth flow.