This research has studied an established Irish retail business as it takes its first tentative steps into the e-commerce arena. Although the adoption of e-commerce is widely studied in the academic world, only a small percentage of these studies focus on the small to medium size enterprise (SME) retail sector. SMEs account for 97% of Irish companies and employ up to 800,000 people (Chamber of Commerce Ireland, 2006). While examining the SME’s adoption of e-commerce, the factors that affected the adoption process were specifically identified and understood. This was achieved by conducting an action research case study. Action research merges research and practice, thus producing exceedingly relevant research findings. This chapter demonstrates how the research was undertaken, and also discusses the justification, benefits, and limitations of using action research. The research concluded that the adoption of e-commerce within the SME sector tends to be slow and fragmented, the presence of a ‘Web champion’ is paramount to the success of the project, and Internet adoption is faster with the recognition of a business need. It also supported the evidence that a SME is more likely to adopt e-commerce when the SME owner has a positive attitude towards IT.