The facilitating effect of the Internet and complementary information and communication technologies on small- and medium-sized enterprises (SMEs) internationalization is now widely accepted. The literature suggests that the Internet positively influences firms' export activities because it provides them with new ways to communicate, to acquire knowledge, to develop their international business network and to improve the efficiency of international transactions and operations. Moreover, emerging Web 2.0 technologies are leading to even more complex international operations. The so-called e-business represents both challenges and opportunities for exporting firms. Given the lack of empirical research into this new paradigm, this research studies professional and business usage patterns of Internet and Web 2.0 technologies and their roles in the pursuit of export market opportunities for Portuguese small- and medium-sized exporters with less than six years of age. Using an online questionnaire, this study is able to identify three ways in which exporting firms use the Internet: as a business tool, as a business enhancer or as a business driver. The empirical results suggest that Portuguese SMEs use the Internet mainly as a business tool, which is essential in the development of export opportunities. Still, using the Internet as a business enhancer and a business driver has a greater impact on firms' export performance. Regarding Web 2.0 technologies, social media has been embraced as a catalyst for export market opportunities development.