During the last decade, E-Gambling commerce has experienced significant economic, technological, political, social and cultural development. It is somewhat surprising given such significance, that there is still a relative scarcity of research conducted or published to date. This research seeks to make an important contribution to addressing such relative neglect by furthering our understanding of the varied complexities associated with the ethics of EGambling commerce. This in-depth study developed a range of theoretical and philosophical approaches to advance knowledge. In terms of theory, this thesis developed ideas in relation to Information Systems Ethics (ISE) and also refers to some developments within Internet and New Media Research (I/NMR) and Interactivity Theory. In terms of philosophical approaches in research this study is broadly Interpretivist and used methods such as interviews, semiotics, virtual ethnography and some secondary evidence. The use of such approaches helped to reveal a range of ethical concerns arising from the commercialisation of EGambling and more importantly the root causes of such issues and consequences. Furthermore, this study of E-Gambling commerce offered some implications for the development of certain theoretical and philosophical approaches.