In high penetrations, demand side management (DMS) applications augment a substation power transformer’s load profile, which can ultimately affect the unit’s capacity limits. Energy storage (ES) applications reduce the evening peaking demand, while time-of-use rates incentivize end-users to charge electric vehicles overnight. The daily load profile is further augmented by high penetrations of photovoltaic (PV) systems, which reduce the midday demand. The resulting load profile exhibits a more flattened characteristic when compared to the historical cyclic profile. Although the initial impact of PV and ES applications may reduce a unit’s peak demand, long-term system planning and emergency conditions may require operation near or above the nameplate rating. Researchers have already determined that a flattened load profile excessively ages a unit’s dielectrics more rapidly. The focus of this research was to identify an approach for establishing new transformer capacity limits for units serving flattened load profiles with a high harmonic content. The analysis utilizes IEEE standards C57.91 and C57.110 to develop an aging model of a 50 MVA SPX Waukesha transformer. The results establish a guideline for determining transformer capacity limits for normal operation, long-term emergency operation, and short-term emergency operation when serving systems with high penetrations of DSM applications.