We describe ongoing work on I2I, a system aimed at fostering opportunistic communication among users viewing or manipulating content on the Web and in productivity applications. Unlike previous work in which the URLs of Web resources are used to group users visiting the same resource, we present a more general framework for clustering work contexts to group users together that accounts for dynamic content and distributional properties of Web accesses which can limit the utility URL based systems. In addition, we describe a method for scaffolding asynchronous communication in the context of an ongoing task that takes into account the ephemeral nature of the location of content on the Web. The techniques we describe also nicely cover local files in progress, in addition to publicly available Web content. We present the results of several evaluations that indicate systems that use the techniques we employ may be more useful than systems that are strictly URL based.