This chapter suggests deepen understanding of civil society regionalization in Southern Africa drawing from what is actually happening on the ground. It explores what factors, both structural and actor-oriented enhance and hinder this process. In terms of the former it is argued that statist and capitalist social structures, reflected by the behaviour of policy-makers within Southern African Development Community (SADC), deeply affect civil society organizations (CSO) for manoeuvre on the regional level. The chapter explains that southern Africa is justified due to the distinct history of civil society interaction in this part of Africa during decolonization and a multitude of state-forms with different links to their respective civil societies. It focuses on the trade sector, where regional civil society engagement is particularly strong. The chapter discusses a theoretical framework for understanding civil society regionalization based on structural and actor-oriented factors. It positions itself within a constructivist approach towards the study of regionalism, which established as the New Regionalism Approach (NRA).