Understanding the age and construction quality of embankments used for road and rail infrastructure is critical in the effective management and maintenance of our transport networks, worth £billions to the UK economy. This paper presents for the first time results from full-scale, carefully controlled experiments on a unique model embankment conducted over the 4-year period between 2008 and 2011. It combines point location and spatially distributed measurements of pore water pressures and water content with outputs from hydrological modelling to draw conclusions of significance to both ongoing research in this field and to the asset management practices of infrastructure owners. For researchers, the paper highlights the crucial importance of transient permeability and soil water retention behaviour of fill materials in controlling the magnitude and distribution of pore water pressure in response to climate and weather events. For practitioners, the work demonstrates that there are significant differences in pore water pressure behaviour across the embankment, which is influenced by construction-related issues such as compaction level, aspect and presence of a granular capping material. Permeability was also observed to vary across the embankment both spatially and with depth, being dependent on degree of saturation and macroscale effects, particularly within a ‘near surface zone’. It is proposed that this ‘near surface zone’ has a critical effect on embankment stability and should be the focus of both ongoing scientific research and inspection and monitoring as encompassed by asset management regimes.