While Electronic Commerce has been touted as the new way in which businesses around the world will operate, there is little research that focuses on small and medium-sized enterprises and the effects that such radical transformation of traditional business processes and practices will have on these small entities. This chapter reports on a practical study undertaken within Australia that focused on small and medium-sized enterprises (SMEs). The specific focus of the study was born out of numerous government reports, which emphasized the advantages of Electronic Commerce and the potential of collaborative, or industry-based practices, to encourage the adoption of Electronic Commerce technologies among these enterprises. The Tasmanian wine sector was investigated in order to identify issues that may inhibit the development of collaborative, industry-wide Electronic Commerce adoption programs. Three issues of significance to these small and medium organizations were identified as: 1) Strategic Orientation and Alignment of members of the sector; 2) Industry Responsibility exhibited by members of this sector; and 3) The Business Case for technology integration.