Although many retail firms from around the world have established a presence in the East African Community (EAC), not all internalization attempts have been successful. Application of the PESTLE model—which examines various political, economic, social, technological, legal, and environmental issues—to investigate the barriers and opportunities in the sector highlights several obstacles to effective and efficient commerce. These include poor infrastructure, inadequate skills and training, and lack of legitimacy. In some cases, these deficiencies also hamper the efforts of locally based retailers to expand in the region. Ultimately, business success may depend on the ability of local governments to design policies and practices that enhance rather than hinder trade and development.