Internet chat-based tutorials are being developed for integrating computer modeling and design skills into mechanical engineering undergraduate and middle school outreach programs. These tutorials help students navigate complicated software interfaces while teaching fundamental concepts through dynamic dialogues between tutorial agents and student user groups. In a typical assignment, students are asked to perform a design or modeling task that includes the use of software such as a commercial finite element code or specially designed educational software. Students work in teams, but team members are distributed within a room or between remote sites, linked by a text interface. As students collaborate electronically, an intelligent agent monitors their interactions and interjects questions or comments in response to the use of key phrases, or due to other triggers. This platform is being used to help automate collaborative learning experiences and to study how students can effectively interact with each other and with the software agents. In undergraduate projects, fundamental technical skills and intuition in interpreting results are emphasized. In outreach efforts, participants are led to consider how their work relates to the broad mechanical engineering profession.