We present ongoing work on systems aimed at improving a user’s awareness of resources available to them on the Internet and in intranets. First, we briefly describe Watson, a system that proactively retrieves documents from online repositories that are potentially useful in the context of a task, allowing the user to quickly become aware of document resources available from online information repositories. Next, we describe I2I, an extension of Watson that builds communities of practice on the fly, based on the work that its users do, so that users with similar goals and interests can discover each other and communicate both synchronously and asynchronously. Both Watson and I2I operate given some knowledge of the user’s current task, gleaned automatically from the behavior of users in software tools. As a result the systems can provide users with useful resources in the context of work they are performing. We argue the systems can foster a greater sense of awareness of the resources available, while minimizing the effort required to discover them.