For the Internet retailers that have managed to dominate through the dot.com fallout, the next step for many is to leverage the technology to expand their operations to a regional or global customer base. However, the internationalization of e-tail differs significantly from traditional retail because of the compounding effect of the Internet, and empirical studies are deficient in the field. This chapter studies the internationalization efforts of three small Internet retail enterprises, highlighting the issues they faced in expanding their operations to service an international customer base. The study reveals their insights and experiences in terms of access to foreign markets, infrastructure considerations, and localization strategies. Through an understanding of these issues, it is hoped that further research will shed light into the intricate relationship between internationalization and Internet retail and the factors that influence it.