The primary objective of this study is to examine the effects of the Internet’s Web tools (the level of Web content and the level of security on the Internet) on the interorganizational relationships (IOR) between small and medium-sized enterprises (SMEs) and their loyal customers. This article focuses on B2B electronic commerce because according to a recent report, the value of goods and services sold via B2B electronic markets will reach $2.7 trillion by the year 2004 (Gartner Group, 2000). While these figures give the impression that B2B electronic commerce is expanding fast, the fact remains that many SMEs are still sitting on the sidelines (Caldeira & Ward, 2002; Lam, Shankar, Erramilli, & Murthy, 2004; Teo, Wei, & Benbasat, 2003). Many SMEs that maintain IOR with their customers have difficulties achieving the benefits as suggested by media and early research (Lituchy & Rail, 2000; Poon, 2000; Tagliavini, Ravarini, & Antonelli, 2001). In addition, there is little existing research that has empirically tested the impact of the Internet’s Web tools on IOR which lead to customer loyalty.