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In 1996, the International Monetary Fund (IMF) and World Bank launched the Heavily Indebted Poor Countries (HIPC) Initiative. The HIPC Initiative is a comprehensive approach to debt reduction designed to ensure that no poor country faces a debt burden it cannot manage (International Monetary Fund, 2011). To date, debt reduction packages providing US $72 billion under the HIPC Initiative have been approved for 36 countries, 32 of them in Africa (International Monetary Fund, 2011). Under the HIPC Initiative, the World Bank and IMF Boards first decide whether or not a country is eligible for debt relief (decision point document). In a second step, all creditors (multilateral, bilateral, and commercial) commit debt relief to be delivered at a “floating” completion point. In between those steps, the country tries to implement the policies determined at the decision point (which are triggers to reaching the completion point). This research paper will examine the HIPC Initiative using a secondary analysis to determine the effectiveness of this program for indebted countries in Africa. The results of this analysis are anticipated to assist in determining weaknesses in debt relief programs, such as the HIPC Initiative, as well as indicate historical economic conditions that set contemporary cycles of debt in motion in Africa.