: In the Anthropocene, hydrological processes and the state of water in different parts of the terrestrial phase of the hydrological cycle can be altered both directly and indirectly due to human interventions and natural phenomena. Adaption and mitigation of future severe droughts need precise insights into the natural and anthropogenic drivers of droughts and understanding how variability in human drivers can alter anthropogenic droughts in positive or negative ways. The aim of the current study was expanding the “observation-modelling” approach to quantify different types of natural and human droughts. In addition, quantifying enhanced or alleviated modified droughts was the second parallel purpose of the research. The main principle of this approach is the simulation of the condition that would have happened in the absence of human interventions. The extended approach was tested in two Iranian catchments with notable human interventions and different climatic conditions. The drought events were identified through hydrological modelling by the Hydrologiska Byråns Vattenbalansavdelning (HBV) model, naturalizing the time series of hydrometeorological data for a period with no significant human interventions, and anomaly analysis. The obtained results have demonstrated that both catchments were almost the same in experiencing longer and more severe negative modified droughts than positive ones because of the negative pressure of human activities on the hydrological system. A large number of natural droughts have also been transformed into modified droughts because of the intensive exploitation of surface and sub-surface water resources and the lack of hydrological system recovery. The results show that the extended approach can detect and quantify different drought types in our human-influenced era.