In the first decade and a half in which the Web has been used for on-line learning, development efforts have centred on putting content on-line. In recent years, however, the challenge has shifted from the need for more content to the need to help teachers and students identify and evaluate authoritative, reliable and verifiable content specific to curricula. The current Canadian sites that either aggregate resources or frame their specific content to curricular needs, however valuable they may be, do not address most of the needs of the teacher in the classroom beset by the problems of preparing lessons quickly and creatively. It has become apparent that teachers need a central site that will rationalize, organize and intelligently link these resources for easier access. Access.ca is an on-line environment, or "teaching space," that allows teachers across Canada to access authoritative Canadian resources, evaluated, tagged and organized for easy retrieval according to their curricular needs. The "gateway" site provides context and meaning for diverse content by creating interconnections and interrelations. Access.ca demonstrates how a deep understanding of users' thought processes, combined with appropriate metadata standards and an effective metadata system, can expose content providers' resources in a manner that makes them truly accessible and useful. This paper discusses the design and technical decisions made in developing access.ca, and the process through by which the developers arrived at those decisions.