Modeling tools are often not used for tasks during the software lifecycle for which they should be helpful; more free-from approaches, such as office tools and white boards, are frequently used instead. Why is this? What might be done to make modeling tools more suitable? What key research challenges must be overcome to achieve this? The goal of this workshop is to bring together people who understand the activities and needs of developers and other stakeholders throughout the software lifecycle, user interface design and tool infrastructure to explore these questions. © 2010 ACM.