The Maloti-Drakensberg (MD) is the largest and highest-elevation mountain system in southern Africa. Covering 40,000 km2 and reaching 3500 m, the MD provides a range of ecosystem services (ES) to the entire southern African region—benefitting diverse users and extending well beyond the mountains. Rapid socioecological change threatens the provision of ES and presents multidimensional challenges to sustainable development. However, the continued land degradation and persisting socioeconomic problems indicate that development policy has not been effective in tackling these issues. In this paper, a multidisciplinary literature review forms the basis of a discussion which takes an ES framing to scrutinise the multidimensional social, political, economic and cultural issues in the study area. Three critical management systems are presented, and their associated ES are discussed, namely, water transfer, rangelands and conservation and tourism. In particular, the diversity of ES uses and values in the MD is considered. The results reveal the main drivers of continued unsustainable development and highlight important information gaps.