The social dimension, commonly referred to as “social sustainability”, has gained more attention recently as a crucial element of long-term success. The majority of previous research on sustainability has focused on economic and environmental problems. On the other hand, as a component of the agenda for sustainable communities and the discourse around urban sustainability, social sustainability has started to excite academic attention as well as political and institutional support. The chapter explains various generalised definitions of social sustainability as a concept being currently applied in various studies and disciplines, which raises a need to have a more specific approach and contextual approach. It asserts that social sustainability assessment methodologies are deficient and builds on the earlier debate over “reductionist” versus “integrated” sustainability evaluation. The research data has been selected from a variety of disciplines, for example, social infrastructure, urban sociology, quality of life, and social sustainability, as a few from the selected ones. The chapter concludes by drawing some key findings that could possibly direct future awareness and advancement within the network of social sustainability and key points to overcome the challenges to assess the progress towards social sustainability.