Organizations, in anticipation of the emergence of Web interface as a major point of contact between companies and customers, are beginning to employ a wide variety of technologies to build meaningful relationships with their customers. While Web interface may not be the only point of contact that customers use, organizations are aware of the advantages of using the Web to cater to the needs of the customers. This concept of “self-service” not only reduces costs for the company in the long run, but also increases customer satisfaction by addressing the transactional and the relational needs of the customer. In this chapter, I review the different types of personalization systems commonly employed by Web sites and argue that their deployment as Web site interface design decisions may have as big an impact as the personalization systems themselves. To accomplish this, I make a case for treating HCI issues seriously and argue that Web site interface design decisions made by organizations, such as the type and level of personalization employed by a Web site, has a direct impact on the communication capability of that Web site. I also focus on the practical relevance of these Web site design decisions by examining their effect on users’ loyalty towards the Web site.