The IGAD region is one of the most important and strategic areas of Africa and the global economy, and possesses potential in natural resources. However, the region remains one of the poorest regions of the World and suffers from a lack of food, not to mention poverty, disease, and continuous internal strife. This paper aims to identify and analyze the common challenges of realizing development in IGAD countries. It employed a qualitative method, using secondary sources. It is found that several factors determine the realization of development in the countries of the region. Though the IGAD region experienced an average annual economic growth, the countries of IGAD are still facing daunting challenges. The region’s development dilemmas include the prevailing unfavorable external environment, crisis of governance, absence of democracy, environmental degradation, disintegration of state services, poor infrastructure, debt, intra- and inter-conflicts, and so forth. It is revealed that the challenges emanate from within and outside the countries and the region that are categorized into social, economic, environmental, and political, or natural and human-made, which are closely intertwined, and they must be reckoned with in tandem. Such challenges can be addressed if the countries of the IGAD are determined to improve their democratic governance.