Many guidelines for portal design tend to focus on the technical aspects of a portal or a network. However, as we continue to define portals as gateways for learning, we need to consider issues related to the social and cultural context in which portals are used. In this chapter we examine learning portals from both the instructors’ and the learners’ perspectives by synthesizing existing research and proposing a framework for quality guidelines. The Collaborative of Online Higher Education Research (COHERE), consisting of eight large research-intensive universities in Canada involved in Internet-based learning, was created to enhance learning and teaching through technology and to move toward a stronger culture of professional collaboration and scholarship in our educational practices (Carey, 2000). Based on our experience with COHERE, we have developed tools for the formative and summative evaluations of learning portals generally. These tools include usability studies, questionnaires and focus groups.