The term lifelong, as applied to education or learning, has been in circulation for more than a quarter of a century. It has played an important role in policy discussions, as well as in studies of the sociology and economics of education. The relationship of this term to the rapidly changing world of information and educational technologies, and to the various conceptions of interaction that are central to these technologies, however, has been considered much less frequently. This paper seeks to shed light on the relationship between lifelong learning and the interactive technologies that have become associated specifically with the Semantic Web. It begins by presenting a fictional narrative to illustrate a lifelong learning scenario in the context of the services and resources that the Semantic Web will be capable of providing. It then proceeds to isolate a number of general characteristics of lifelong learning as they are manifest in this scenario and in recent literature on the subject. The paper then explores how emergent, interactive technologies of the Semantic Web have the general potential to address many of the characteristics of lifelong learning, and hold out the promise of satisfying a wide variety of lifelong learning needs. It will conclude by considering some of the outstanding challenges presented by lifelong learning contexts, and mention some of the limitations of advanced technologies used to address these needs.