In the Southern African Development Community (SADC), the majority of people, especially women, continue to deal with the risks in their lives with limited state support. At the same time, women subsidize most of the formal social security systems despite exclusion and exploitation. Survival mechanisms operate within complex plural regulatory frameworks that engender social security and/or insecurity. A number of efforts in the SADC region are intended to harmonize the regulation of social security and to extend coverage of social security to excluded groups such as women. This article highlights the challenges to harmonization of the regulation of social security in the SADC region from a gendered perspective. By focusing on the Charter for Social Protection in SADC, the article discusses how efforts to harmonize the regulation of social security takes a legal centralist approach that fails to reflect the realities of the majority of women, thus not achieving the objective of transforming social security for the benefit of the majority. The article argues that unless the harmonization process reflects this reality, it will only perpetuate the gap between practice and rhetoric and the exclusion of women from social security systems. Harmonization efforts need to take account of the plurality of the legal and social security systems and their different impact on men and women.