The development of digital technologies is accelerating, enabling increasingly profound changes in increasingly short time periods. The changes affect almost all areas of the economy as well as society. The energy sector has already seen some effects of digitalization, but more drastic changes are expected in the next decades. Besides the very positive impacts on costs, system stability, and environmental effects, potential obstacles and risks need to be addressed to ensure that advantages can be exploited while adverse effects are avoided. A good understanding of available and future digital applications from different stakeholders’ perspectives is necessary. This study proposes a framework for the holistic evaluation of digital applications in the energy sector. The framework consists of a combination of well-established methods, namely the multi-criteria analysis (MCA), the life cycle assessment (LCA), and expert interviews. The objective is to create transparency on benefits, obstacles, and risks as a basis for societal and political discussions and to supply the necessary information for the sustainable development and implementation of digital applications. The novelty of the proposed framework is the specific combination of the three methods and its setup to enable sound applicability to the wide variety of digital applications in the energy sector. The framework is tested subsequently on the example of the German smart meter roll-out. The results reveal that, on the one hand, the smart meter roll-out clearly offers the potential to increase the system stability and decrease the carbon emission intensity of the energy system. Therefore, the overall evaluation from an environmental perspective is positive. However, on the other hand, close attention needs to be paid to the required implementation and operational effort, the IT (information technology) and data security, the added value for the user, the social acceptance, and the realization of energy savings. Therefore, the energy utility perspective in particular results in an overall negative evaluation. Several areas with a need for action are identified. Overall, the proposed framework proves to be suitable for the holistic evaluation of this digital application.