Previous research has identified that small business faces additional barriers to e-commerce adoption compared with large business. More recently it has emerged that the adoption of e-commerce technology has often not translated into the active utilisation and conduct of e-commerce by small business. The factors and problems that account for this apparent lack of benefit derived from e-commerce activity forms the focus of this chapter. This chapter identifies and critically analyses the range of factors impacting on small businesses conducting e-commerce. A framework is developed to explore potential problem areas for e-commerce implementation and utilisation. This framework is based upon a qualitative analysis of 34 Australian SMEs utilising e-commerce and from findings in a report conducted by Ernst & Young of an additional 34 Australian small businesses implementing e-commerce. The chapter endeavours to provide an outline of the issues that policymakers need to consider in developing e-commerce policy to motivate and support ongoing e-commerce initiatives among SMEs.