Much has been written about the inability of Small and Medium Enterprises to catch the e- Commerce train. This research attempts to delve directly into the motives of Micro- Enterprises decision-makers with a set of interpretive case studies. The rationale for using qualitative research is that since it is about technology and business needs, techniques commonly used in system analysis and requirements gathering can be a natural fit. Although the stories are reminiscent of SME situations in other parts of the world, they reveal that New Zealand Micro-Enterprises willing to set-up e-Commerce ventures struggle with a unique local blend of obstacles. What is revealed is that decision makers operate in a macrocosm, and are influenced by their peers, business partners, suppliers and even competitors.