All around the world, inequalities persist in the complex web of social, economic, and ecological factors that mediate food security outcomes at different human and institutional scales. There have been rapid and continuous improvements in agricultural productivity and better food security in many regions of the world during the past 50 years due to an expansion in crop area, irrigation, and supportive policy and institutional initiatives. However, in Sub-Saharan Africa, the situation is inverted. Statistics show that food insecurity has risen since 2015 in Sub-Saharan African countries, and the situation has worsened owing to the Ukraine conflict and the ongoing implications of the COVID-19 threat. This review looks into multidimensional challenges to achieving the SDG2 goal of “End hunger, achieve food security and improved nutrition, and promote sustainable agriculture” in Sub-Saharan Africa and the prosper policy recommendations for action. Findings indicate that weak economic growth, gender inequality, high inflation, low crop productivity, low investment in irrigated agriculture and research, climate change, high population growth, poor policy frameworks, weak infrastructural development, and corruption are the major hurdles in the sustaining food security in Sub-Saharan Africa. Promoting investments in agricultural infrastructure and extension services together with implementing policies targeted at enhancing the households’ purchasing power, especially those in rural regions, appear to be essential drivers for improving both food availability and food access.