Africa represents one of the fastest-growing consumer markets in the world driven by urbanization, demographic expansion, digital retail adoption, and rising middle-income households. However, global retail brands face significant barriers when entering African markets due to infrastructural gaps, regulatory fragmentation, supply chain inefficiencies, currency instability, and cultural heterogeneity. This study assesses key obstacles to retail expansion across Africa through mixed-method research including retailer case analysis, policy document review, and interviews with local market experts. Findings reveal that logistics constraints, informal market dominance, inconsistent regulatory environments, and limited cross-border trade integration are the primary inhibitors. A multi-layered strategic framework is proposed to support scalable retail market entry.