Part of efficient management is measuring actual performance against desired metrics. In turn, actual strategic outcomes can be measured against plan. The authors show that this is also true of organizations’ e-commerce performance versus planned performance. While most organizations with successful e-commerce tend to take the view “There’s no stopping us now!,” the authors explore the interesting relationship between what the organizations had originally intended versus what operations actually dictated and how those changes affected their sites’ performance. To add to the literature, the authors explore the ramifications of the results of a survey conducted among some of the leading organizations in today’s business and the analysis of several dot.com enterprises. Along the journey, the authors discovered changes in organizations’ “desired capability” occurred as the organizations encountered various challenges to their global e-commerce, such as currency fluctuation and logistical considerations involved with order fulfillment, from industrially powerful countries versus third world countries. The authors also explore various aspects of organizational change evidenced when organizations entered into e-commerce globally. The authors show that theoretical approaches quite often must change with the realities of business when organizations commence e-commerce operations.