In this chapter we have attempted to improve the understanding and management of an important strategic element known as customer switching costs. By reviewing the strategy, economics, and marketing literature, we show that researchers have long acknowledged the importance of the phenomenon. In addition, we discuss how switching costs appear to be changing as a result of the increasingly networked environment. Despite broad recognition of its important and changing strategic role, we find a lack of coherence and comprehensiveness regarding the conceptualization of switching costs and the tools or models provided to manage the force. To address these issues we attempt to build upon and refine the term’s conceptualization and we developed an integrated switching cost framework, mainly focused on positive switching costs stemming from Web sites’ elements. We believe that the switching cost framework provides a powerful and insightful lense for managers pursuing competitive advantage in today’s networked environment. But, despite the importance of a Web site, the process of designing high quality Web sites for e-commerce is still more of an art than a science. E-commerce companies still rely largely on intuition when it comes to designing their Web sites. To make matters worse, design changes and their impacts are not tracked, making it impossible to measure the benefits of Web site design (Wallach, 2001). This situation brings to the foreground the importance of value-driven evaluation and design of e-commerce Web sites. However, e-businesses are facing difficulties due to the lack of proven tools and methods for accomplishing this. Customers expect a certain level of service to accompany their purchases of goods and services. At the same time, in a digital environment, customers expect to enjoy a satisfying online shopping experience: changing Web surfers into loyal customers has thus become the final goal of many online firms. Moreover, elements that contribute to customer satisfaction and to the creation of a customer feeling of positive switching costs and thereby lead to repeat purchases include availability of sufficient information, ease of use interfaces, general Web site usability, simplicity in the interface design, deep customer service, etc. Yet, the Web-based retail shopping experience may differ from conventional shopping in several ways, possibly resulting in differing customer satisfaction elements. With the explosive growth of conventional marketers offering their products and services online, as well as new businesses proliferating solely for online marketing, research is warranted to examine the key factors in customers’ shopping experiences that contribute to customer satisfaction with shopping via this new marketing channel. Research that contributes to an understanding of customer experiences with online shopping has important implications for researchers as well as business managers and information systems managers (Adam et al., 1999). Although marketers are beginning to understand the innovative strategies that will attract visitors to Web sites (Hoffman et al., 1995), little is known about the factors that make Web use a compelling customer experience or about the key customer satisfaction outcomes of this compelling experience. Researchers have been trying to develop and test a general model of the online customer experience (Novak and Hoffman, 1997; Novak et al., 2000). However, few studies have been conducted to test the relationship between retail Web site presentations and key elements of customers’ actual online shopping experience (in terms of site design effectiveness for satisfactory customer shopping experiences). Conventional marketing research has illustrated the relationship of customer service variables with customer outcomes such as customer satisfaction (Bolton & Drew 1991; Fram & Grady 1995; Zeithaml & Berry 1993). Customer satisfaction or dissatisfaction is the core concept of marketing and information systems (Kosiur, 1997). It follows that lack of satisfaction with a Web site would lead to customer intention not to purchase from that site. Accordingly, this research attempts to analyze some elements of online shopping experiences that influence the shopper’s satisfaction with the online shopping experience, leading the shopper to purchase from that site or alternatively to switch to another site.