Belonging to one or more regional blocks is very popular in Africa as could be seen from the plethora of multiple membership of countries. South Sudan is no exception in such effort. The purpose of this research is to assess the extent to which the Republic of South Sudan will likely benefit (in the short, medium and long-run) from joining any trading arrangements with the existing trading blocks in Africa, but particularly in one of those in Eastern Africa. This research, therefore, has three broad interrelated parts based on three main objectives; The first category focuses on the state of regional integration and the South Sudan economy. The Second section evaluates the retrospect and prospects of regional integration in South Sudan; this will include reassessing when, under what conditions, and how a new independent country should pursue the integration process with its actual and potential partners. The third and final section will address the possible contributions and challenges, and suggest the most optimal approach(s) that a country like South Sudan should follow in evaluating the intertemporal pros and cons of joining such grouping given the state of their economies.