In petroleum industry, the difference between pore pressure (Pp) and minimum horizontal stress Sh (termed the seal or retention capacity) is of major consideration because it is often assumed to represent how close a system is to hydraulic failure and thus the maximum hydrocarbon column height that can be maintained. While Sh and Pp are often considered to be independent parameters, several studies in the last decade have demonstrated that Sh and Pp are in fact coupled. However, the nature of this coupling relationship remains poorly understood. In this paper, we explore the influences of the spatial pore pressure distribution on Sh/Pp coupling and then on failure pressure predictions and trap integrity evaluation. With analytical models, we predict the fluid pressure sustainable within a reservoir before failure of its overpressured shale cover. We verify our analytical predictions with experiments involving analogue materials and fluids. We show that hydraulic fracturing and seal breach occur for fluid pressure greater than it would be expected from conventional retention capacity. This can be explained by the impact of the fluid overpressure field in the overburden and the pressure diffusion around the reservoir on the principal stresses. We calculate that supralithostatic pressure could locally be reached in overpressured covers. We also define the retention capacity of a cover (RC) surrounding a fluid source or reservoir as the difference between the failure pressure and the fluid overpressure prevailing in shale at the same depth. In response to a localized fluid pressure rise, we show that the retention capacity does not only depend on the pore fluid overpressure of the overburden but also on the tensile strength of the cover, its Poisson's ratio, and the depth and width of the fluid source.