Many small and medium sized businesses (SMEs) have set up their own Web sites, as part of their business strategies, to improve their competitiveness and responsiveness. Careful evaluation and adoption of Web sites by SMEs can assist them in improving the effectiveness of their venture into e-commerce. This chapter discusses and analyses the effectiveness of SME business to business Web sites from a user perspective. An effective method of evaluating a Web site can contribute to the development of more quality Web sites and greater realization of benefits. Therefore, an established evaluation instrument (eQual) is used to assess 80 Web sites in terms of usability, information quality, and interaction and service. The analysis shows that although a significant number of sites reflect little understanding of the attributes of good design or potential benefits to be gained from Web sites, there are examples of competent and effective Web site use.