Australian small businesses are increasingly adopting the Internet and the World Wide Web as a medium of doing business to reach new customers and suppliers, cut costs and expand business. They also use it to enhance communication between buyers and suppliers. This chapter discusses the findings of an exploratory study in Australia that identified the objectives, opportunities and challenges of e-commerce experienced by small businesses that were mostly early adopters of the Internet as a medium of trade. E-commerce issues presented in this chapter include research findings, supported by theory from literature. Electronic commerce opportunities, challenges and organizational learning by small and medium enterprises (SMEs) in Australia indicate that small businesses have created value with e-commerce, although benefits are long term and dependent on a plethora of technological, business and management issues that need to be addressed. Due to the fast-evolving nature of e-business and technological developments that are new to many small businesses, challenges such as managing the expanded flow of information, cross-border taxation, authentication, trust and security, as well as the high costs of acquiring the required technologies and skills, are prevalent. Other challenges of e-commerce range from Web site maintenance to business process reengineering for an integrated environment. Research findings also highlight the fact that small businesses need formal methods of evaluating the performance of e-commerce to realize the benefits of investment and to further expand their e-commerce venture.