Cement-based columns in combination with geosynthetic reinforcement is a well-established soft ground improvement technique to enhance embankment stability. This paper aims to present a finite-element (FE) study based on a case history of a geosynthetic-reinforced column-supported (GRCS) embankment over soft soil. In this study, the columns are simulated with an advanced Concrete model to simulate the development of possible cracking and induced strain-softening. Numerical results are compared against published centrifuge tests, giving confidence to the established FE model with the Concrete model. New insights into the progressive failure mechanisms of GRCS embankments over soft soil are then discussed by examining the stress paths, internal forces, and cracks, as well as the plastic failure zones of columns. In addition, the role of columns and geosynthetics on the progressive failure mechanisms (failure loads and sequences) is also examined by an extensive parametric study. The results suggest that provided the optimization of compressive and tensile forces in the columns combined with the tensile stiffness of the geosynthetics is put in place, more columns can be mobilized to resist global sliding failure and to improve the bearing capacity of GRCS embankments.