Soil moisture is crucial to water-cycle as it affects infiltration, runoff and land-atmosphere interactions. In dry soils the role of water vapor fluxes becomes essential and causes a tight coupling between soil moisture dynamics and heat transfer, which makes measurements and modeling extremely difficult. Since advances in both theory and experimental techniques are required, we have focused on both aspects: we have performed theoretical-numerical investigations of soil moisture and energy dynamics at the land surface; tested novel measurements techniques, in laboratory and at field scale, to provide new insights into soil moisture dynamics and contribute to a comprehensive theory of coupled energy and moisture transport. As the dynamics of physical systems are dictated by conservation equations, it is common practice to estimate quantities that cannot be directly measured (e.g. vapor fluxes) from the residuals of balance equations. In laboratory as well as in field experiments, residuals are calculated from measurements that are sparse in space and discrete in time. We have theoretically and numerically shown how the use of discrete data may lead to large residuals even without measurements or model errors. We have demonstrated that residuals are very sensitive to the distance between the measurements and that they increase in presence of nonlinear processes, such as moisture transport. A careful error analysis is required to assess the reliability of residuals computed from discrete data and avoid misinterpretations of the underlying physical processes. Another crucial element dictating soil moisture dynamics and evaporation into the atmosphere is soil water-retention. Popular parametric models of the retention curve present a matric potential that becomes infinite at residual saturation, which is the water content below which liquid flow stops. Few extensions of the water-retention curves have been proposed, which remain rarely used in practice. We have studied the effects of different models on liquid and vapor transport. We have shown that parameterizations that allow vapor flux below residual saturation yield larger vapor fluxes that result in a drier soil surface, whereas deep soil remains relatively wet. When diurnal forcing is considered, potential evaporation is reduced in the energy-limited regime and enhanced in the moisture-limited regime. We have established that in this case extended water-retention models predict larger heat fluxes that might critically impact models at whole scales (possibly including global circulation models). Discrimination between different theoretical descriptions and parametric models requires experiments that monitor moisture and energy dynamics. This demands the use of accurate sensors and measurement techniques that are able to simultaneously monitor several quantities (e.g. soil moisture, temperature, soil thermal properties, solute concentration in soil water). As in general different probes are used, problems arise due to different footprints and sampled soil volumes. Multi functional heat pulse probes (MFHPPs) have been conceived to overcome these issues by allowing simultaneous measurements of all required variables. We have assessed MFHPPs ability to measure ground heat flux, which has to be accurately known to avoid significant imbalances in the surface energy budget. We have employed an experimental setup able to generate a non-uniform heat-flux field and we have demonstrated that MFHPPs can reliably capture the magnitudes and directions of the fluxes. This allows more complete information on ground heat flux than that obtained by the classic probes (e.g. ground heat flux plates). To monitor soil state in large-scale field applications we have investigated the possibility to infer distributed thermal conductivity and soil moisture profiles with an optical fiber. Information is obtained by monitoring soil response to an active heat pulse generated from the metal shield armoring the optic cable, and analyzing the temperature differences of the cooling phase, monitored each meter by a distributed temperature sensing system (DTS). We have shown that soil moisture measurements inferred from soil thermal response (recorded by the DTS) are in good agreement with independent measurements in wet and intermediately wet soils; however in dry soils moisture content is underestimated and further investigations are required to improve this technique for dry conditions. In this study we have significantly improved the knowledge of coupled energy and moisture transport on both theoretical-numerical and experimental sides. We have proven that reliable measurements can be obtained at different spatiotemporal scales, and provided both prognostic and diagnostic methods to optimize their use. Finally, we have suggested crucial improvements to numerical models which might have implications beyond field-soils dynamics.