In this work, a holistic energy management methodology comprising forecasting and scheduling algorithms was developed. The algorithms aim at maximizing the customer benefits during normal operation as well as supplying critical infrastructure during grid events. Four separate real-world trials were conducted over a period of three months in the context of a demonstration in an MV customer with results showing that energy costs may be reduced to up to 27.3% while also dropping the system’s peak load demand by up to 16.7%. In terms of islanding capabilities, the trials demonstrate the system’s ability to support the local network during blackouts and suggested the need for a formalization and standardization of the sizing process of any equipment with blackout capabilities within the planning of LV/MV systems. Additional use cases that aim at unveiling the flexibility offered to aggregators were examined and results showed that the proposed scheme can support flexibility services during Demand Response (DR) events.