Using a case-study approach, this chapter aims to assess the development issues for e-business within small to medium enterprises (SMEs) in differing regions across the UK. The research documents the issues faced by three SMEs as they have embarked upon an e-business delivery. All of the case studies are SMEs that come from different industry sectors, but all have established an e-commerce service in the last 18 months. Our definition of e-commerce aligns with those principles set out by the Organisation for Economic Cooperation and Development (OECD) working party on Indicators for the Information Society WPIIS. The outcome is an evaluation and discussion of the underlying factors influencing each company’s progress within a regional UK framework. Issues raised in the study include lack of training and awareness in SMEs, the need for government-funded initiatives, reliance on personal networks, and a lack of clarity about funding sources and schemes.