Numerous models have been developed to aid in the decision making process to identify the most suitable energy provision options for a given community or area. Some models focus strictly on one key planning aspect, such as cost or technology (single-criteria decision analysis), while other models take multiple criteria into consideration, such as cost and technology, social, human and environmental factors (multi-criteria analysis). This chapter aims to show that the inclusion of multiple technical and non-technical criteria can lead to more sustainable development outcomes. To do so, it provides a comparison between several single factor and multi-criteria models, highlighting their applications and limitations in the context of rural energy planning in developing countries. This is followed by a discussion of the factors that should be considered to ensure optimal service provision,, long-term sustainability of rural electrification projects and poverty alleviation. The subsequent section introduces and analyses the components of the Sustainable Rural Energy Decision Support System (SURE-DSS) approach and methodology. The novelty of the SURE tool lies in its objective to match rural community's energy needs in developing countries to appropriate technologies and thereby improve livelihoods and project sustainability. The chapter explains the approach and illustrates the tool's application through a case study in Colombia.