Software design, development, and maintenance constitute a complex and time-intensive process. Early design decisions can have a crucial impact on both quality and cost. Design rationale tools have been shown to be effective in supporting this process, but are infrequently used due to their interference with normal design team workflow. The rapid growth of new network and web-mediated workstyles offers the opportunity to bring design rationale tools into normal workflow. However, existing tools require the designer to think in terms of the structures the tools provide. Further, few are integrated into modern net-mediated workflows which emphasize shared workspaces and rapid, asynchronous email exchanges. Full acceptance of such tools requires reduction of the data entry burden they impose. We believe that through restricted use of natural language understanding and full text information retrieval, we can bridge the gap between the specialized notations typically used in design rationale systems and the informal discussion that typifies dialog among design team members. We propose a thorough study of the opportunities for integration of these technologies into a design rationale tool, followed by detailed design and partial prototyping of the key capabilities we identify.