The Web’s linking of information has alluring effects on the curious: starting from a page, we can click through to anywhere in the world. Many people can recall occurrences of online serendipity—when they coincidentally found something interesting when looking for something completely different. Yet, not everything on the Web works this way. Especially for machine clients, who are currently bound to rigid interaction patterns, using the Web in a flexible and dynamic way remains difficult. This chapter therefore explores the possibilities to achieve serendipitous applications.