We utilize event-by-event Monte Carlo simulations within the JETSCAPE framework to examine scale-dependent jet-medium interactions in heavy-ion collisions. The reduction in jet-medium interaction during the early high-virtuality stage, where the medium is resolved at a short distance scale, is emphasized as a key element in explaining multiple jet observables, particularly substructures, simultaneously. By employing the MATTER+LBT setup, which incorporates this explicit reduction of medium effects at high virtuality, we investigate jet substructure observables, such as Soft Drop groomed observables. When contrasted with existing data, our findings spotlight the significant influence of the reduction at the early high-virtuality stages. Furthermore, we study the substructure of gamma-tagged jets, providing predictive insights for future experimental analyses. This broadens our understanding of the various contributing factors involved in modifying jet substructures.