The granular column collapse experiment is an important benchmark case for the physical and numerical study of transitional mass flows. Unlike columns of dry granular materials, the presence of a relatively incompressible fluid, such as water, in the voids of saturated columns complicates the shear behavior of the column by becoming a function of the coupled shear and volumetric behavior of the grain–fluid system. Dilative or contractive behavior at the pore level will cause a decrease or increase, respectively, in the pore fluid pressure. These changes in effective stress, in turn, will define stability or instability and length of runout. Here we use the new opportunity provided by transparent soil to observe air entry within saturated columns to explore the hypothesis that the entry pressure provides the maximum contribution of capillary pressure at incipient failure, thereby providing a quantitative control on the stability of dilative granular columns. Furthermore, the mobility of densely packed saturated columns subject to collapse was significantly influenced by air entry. An analytical model, based on this assumption of limiting capillary pressure, is able to describe the stability of the experimental columns as well as the larger dataset from the literature, reframing the previous empirical stability threshold using limit equilibrium and soil material parameters. Our results demonstrate the importance of stress-dilatancy and air-entry phenomena on the rapid shear behavior of saturated granular materials.