Subsurface volume loss takes place in many geotechnical situations, and it is inherently accompanied by complex stress and displacement fields that may influence the performance of engineered geosystems. This research is a deformation-centered analysis, it depends on soil compressibility and it is implemented using finite elements. Soil stiffness plays a central role in predicting ground deformation. First, an enhanced Terzaghi’s soil compressibility model is proposed to satisfy asymptotic conditions at low and high stress levels with a small number of physically meaningful parameters. Then, the difference between small and large strain stiffness is explored using published small and large-strain stress-strain data. Typically, emphasis is placed on the laboratory-measured stiffness or compressibility; however, there are pronounced differences between laboratory measurements and field values, in part due to seating effects that prevail in small-thickness oedometer specimens. Many geosystems are subjected to repetitive loads; volumetric strains induced by drained repetitive ko-loads are experimentally investigated to identify shakedown and associated terminal density. The finite element numerical simulation environment is used to explore the effect of localized subsurface mass loss on free-surface deformation and shallow foundations settlement and bearing capacity. A stress relaxation module is developed to reproduce the change in stress associated to dissolution features and soft zone formation. The comprehensive parametric study is summarized in terms of dimensionless ratios that can be readily used for engineering applications. Field settlement data gathered at the Savannah River Site SRS are back-analyzed to compare measured values with predictions based on in situ shear wave velocity and strain-dependent stiffness reduction. The calibrated model is used to estimate additional settlements due to the pre-existing cavities, new cavities, and potential seismic events during the design life of the facility.