This paper presents a comparative analysis of social insurance systems in Egypt, Jordan, and Tunisia. It examines legal, structural, and institutional distinctions and investigates efforts to extend coverage to challenging-to-insure groups and sectors. Conceptualized within the framework of the social contract, the analysis takes a two-pronged approach. Firstly, a mapping of the legal provisions and de jure coverage of social insurance schemes is conducted for all three countries to assess the inequalities in access to contributory social insurance schemes and identify vulnerable groups at risk of exclusion due to labor market dynamics and economic structures. Secondly, de facto social insurance coverage is explored by analyzing data from the Integrated Labor Market Panel Surveys (ILMPS) for Egypt (2018), Jordan (2016), and Tunisia (2014). The analysis reveals that in all three countries, gaps are present between de jure and de facto social insurance coverage. This is especially true for those engaged in sectors characterized by high informality, daily wage laborers, women, youth, and low-income individuals. Additionally, significant gaps persist between the private sector and the public sector. The findings underline the need for a comprehensive approach to foster inclusivity in the social insurance system, which can significantly upgrade the broader social contract.