In the last decades, the use of mechanical action to exploit chemical transformations has proven to be the key for the discovery of unique reactivities and selectivities. In this context, and aided by their intrinsic values of sustainability, mechanochemical approaches have found success in fields such as organic synthesis, polymeric materials, supramolecular chemistry, and waste valorization. Despite this spread growth, the understanding of mechanochemical transformations at a molecular level and the impact that mechanical forces have on the properties of the milled material is still in its infancy. Apparently, the physical constraints of the machinery used to induce mechanochemical reactivities by grinding limit the in situ monitoring approaches to the use of a few ad hoc techniques, mainly being Raman spectroscopy and powder X-ray diffraction (PXRD). Alongside these, other approaches involving solid state nuclear magnetic resonance (NMR) spectroscopy have been considered because of its detailed information at a molecular level, but the complexity of the required machinery for the analyses have severely limited its use when combined with the grinding action of milling devices. In the solid state, molecular interactions between different species result in co-crystalline compounds with altered physico-chemical properties compared to their initial single components. Consequently, properties such as solubility, melting point, and stability to degradation can vary. An analogous behavior is observed for mixtures of stereoisomers of the same chemical species. There, it is the basis of widely used enantiopurification protocols by sequential crystallizations and spontaneous disproportionations occurring during achiral chromatography, distillation, or sublimation. These last phenomena, despite having the same result of an amplification of optical purity without variations in the chirality of single molecules, depend on the type of physico-chemical process applied and their causes remain largely unexplored. Regrettably, such lack of knowledge is in sharp contrast with the general importance that selfdisproportionation of enantiomers (SDE) can have in purification applications and in explaining prebiotic chirality and homochirality. In addition, the little attention that is given to the specific topic of SDE by sublimation can have implications in the reliability of optical evaluations. We hypothesized that ball milling, with its characteristic of ensuring a constant distribution of the milled solids and enhancing solid-solid interactions could be the key for unprecedent insights in SDE by sublimation. More generally, we expected this idea to lead to exploring and controlling the relations that subsist between the characteristics of the milled solids and their sublimation.