The emergence of Web 2.0 technologies and associated services heralded a second generation of the Internet emphasising collaboration and sharing amongst users. This resulted in a seismic shift in the relationship between individual consumers and firms but also between individual consumers and the Internet as a system. Consumers, not firms, became an emerging locus of value production and through the ability to publish and connect with known and unknown others, an emerging locus of power (Berthon, Pitt, Plangger, & Shapiro, 2012). Powered by broadband telecommunications and device connectivity, the intensity of these changes was further deepened by being freed from the desktop to the mobile web. We are more connected now than ever before. The high levels of societal interconnectedness encouraged by the internet have made trust an even more vital ingredient in today’s society (Hardin, 2006). The more recent development of Web 3.0 technology emphasises ubiquitous connectivity and a machine-facilitated understanding of information that may once more change the locus of activity, value production and control. In order to keep pace with the issues of contemporary society, trust researchers must consider the how trust relationships and perceptions operate and are influenced by the online environment. This chapter will discuss how traditional trust concepts translate to the online context and will examine empirical literature on online trust at three different levels. Interpersonal trust between individuals using the internet as a medium for communication is particularly relevant in a world where personal and professional relationships are increasingly mediated by technology. We will also discuss the role of the internet in relationships between individuals and organisations with particular attention to the provision of e-services. Finally, we discuss trust in the system of the internet itself as a distributed connected infrastructure made up of indirect system service providers which are often nameless or in the background. Our focus in the chapter is on individual trust in other individuals, organisations and the system of the internet itself. Trust from the perspective of the organisation may also be of interest to trust scholars. This includes issues relating to organisational trust in individuals, inter-organisational trust, and organisational trust in the system of the Internet itself however these topics are outside of the scope of this chapter (see Perks & Halliday, 2003; Ratnasingam, 2005).