AbstractAmong the different noncovalent interactions, halogen bonds have captured wide attention in the last years. Their stability has been rationalized in electrostatic terms by appealing to the σ‐hole concept, a charge‐depleted region that is able to interact favorably with electron rich moieties. This interpretation has been questioned, and in this work a set of anionic halogen model systems are used to shed some light on this issue. We use the interacting quantum atoms method, which provides an orbital invariant energy decomposition in which pure electrostatic terms are well isolated, and we complement our insights with the analysis of electrostatic potentials (ESPs) as well as with traditional descriptors of charge accumulation like the Laplacian of the electron density. The total electrostatic interaction between the interacting species is surprisingly destabilizing in many of the systems examined, demonstrating that although σ‐holes might be qualitatively helpful, much care has